Arylhalide-Tolerated Electrophilic Amination of Arylboronic Acids with N-Chloroamides Catalyzed by CuCl at Room Temperature

Size: px
Start display at page:

Download "Arylhalide-Tolerated Electrophilic Amination of Arylboronic Acids with N-Chloroamides Catalyzed by CuCl at Room Temperature"

Transcription

1 Current Literature July 19, 08 Jitendra Mishra Arylhalide-Tolerated Electrophilic Amination of Arylboronic Acids with -Chloroamides Catalyzed by CuCl at Room Temperature Aiwen Lei et.al. College of the Chemistry andmolecular Sciences Wuhan University Wuhan, Hubei, (PR China) Angew. Chemie. Int. Ed. 2008, Early view Jitendra Wipf Group Page 1 of 20 7/22/2008 1

2 Introduction Aryl amines are common place in chemistry. Arene-nitrogen or arene-oxygen linkage is included in nitrogen or oxygen heterocycles such as Indole, and benzofurans. Isodityrosine based natural product such as vancomycin. Conjugated polymers such as polyanilines. Readily oxidized triarylamines used in electronic applications such as such as,'-diphenyl-,'-bis(3-methylphenyl)- 1,1'-biphenyl-4,4'-diamine. Jitendra Wipf Group Page 2 of 20 7/22/2008 2

3 Historical Background: The initial effort for the formation of transition metal mediated C- bond was made by Hartwig et. al. and Buchwald group independently. Br + Bu 3 SnR 2 [(o-ch 3 C 6 H 4 ) 3 P]PdX % R 2 Hartwig et. al. JACS 1994, Jitendra Mishra@ Wipf Group Page 3 of 20 7/22/2008 3

4 Br R' R + HRR' L 2 Pd or L 2 PdCl 2 Li(SiMe) 3 30 min. 60 o C Hartwig et. al. TL 1995, First tin reagent free Pd catalyzed amination of aryl halide. Jitendra Mishra@ Wipf Group Page 4 of 20 7/22/2008 4

5 Br R' R R + HRR' L 2 Pd or L 2 PdCl 2 tbuoa o C, toluene, 71-89% R X HBn n Cat. Pd aotbu, K 2 CO 3, Toluene, 100 o C, % n Bn n = 1-3 Buchwald et. al. Angew. Chem. Int. Ed. 1995, 1348 Jitendra Mishra@ Wipf Group Page 5 of 20 7/22/2008 5

6 Jitendra Wipf Group Page 6 of 20 7/22/2008 6

7 H 2 COOH + ArX CuI K 2 CO 3, DMA, 5-92% H COOH Possible catalytic cycle Dawai Ma et. al. JACS 1998, Jitendra Mishra@ Wipf Group Page 7 of 20 7/22/2008

8 CuSO 4, Cu(OAc) 2, CuI, were used as catalysts and gave over 80% yield. The reaction catalyzed by CuI was faster comparision to other. A strong o-carboxylate accelarating effect was observed while p- has no similar effect. The order of halogen displacement from aromatic ring is I > Br > Cl. Amino acid containing larger hydrophobic group gave higher coupling yield compare to lower hydrophobic group and the amino acids with hydrophillic group yielded no coupling product at all. Cyclic amino acid gave higher yield. Jitendra Mishra@ Wipf Group Page 8 of 20 7/22/2008 8

9 Ar-I + O H R' R 1 mol% CuI, 10 mol% ligand, O 2 eq K 3 PO 4 23h, 110 o C, Dioxane Ar R' R RH Ligand HR R 1 mol% CuI, I + R 2 R 3 10 mol% ligand, 2 eq K 3 PO 4 H 24h, 110 o C, Dioxane, R % R 3 R 2 1a; R = H 1b; R = Me - -arylation of nitogen heterocycles Buchwald et. al. JACS 2001, Jitendra Mishra@ Wipf Group Page 9 of 20 7/22/2008 9

10 O R O H 2 L-amino ester B(OH) 2 Cu(OAc) 2, TEA, 4A o MS, DCM, rt, 1-2 days R H O O Lam et.al. TL 2003, 1691 Jitendra Mishra@ Wipf Group Page 10 of 20 7/22/

11 Jitendra Wipf Group Page 11 of 20 7/22/

12 O H + B(OH) eq Cu(OAc)2, 1.1 eq oxidant, TEA 4A o MS, DCM, rt, air, 1-2 days O Pyridine-oxide > TEMPO > MO > di-t-butyl nitroxide > (1R) (10-camphor- 69% 64% 62% 55% 48% sulfonyl)oxaziridine > abo 3.H 2 O, > K 3 Fe(C) 6 > mcpba 31% 11% 6% Lam et. al. TL 2001, 3415 Jitendra Mishra@ Wipf Group Page 12 of 20 7/22/

13 Ph OR' Ph + Ph B(OH) 2 10 mol% CuCT solvent, Ar, 50 o C, 3h Ph Ph Ph Cross-coupling product + Ph Ph + Homocoupling O Ph Ph Hydrolysis CuCT = Cu(I) thiophene-2-carboxylate Liebeskind et.al. 2007, Jitendra Mishra@ Wipf Group Page 13 of 20 7/22/

14 Ar O + CuCl 1. DMF, 55 o C, min eq Ar'B(OH) 2, DMF, 55 o C, 16h Ar H Ar' Liebeskind et. al. OL. 2004, 2631 Jitendra Mishra@ Wipf Group Page 14 of 20 7/22/

15 Title paper: Reasons to Choose -Chloroamides: - Ease of preparation of -Chloroamides. - High activities of -Cl bond. R 1 R 2 H aox/ter-buoh AcOH/MTBE 0 o C, 15 min-2h, % R 1 R 2 X X = Br, Cl Jitendra Mishra@ Wipf Group Page 15 of 20 7/22/

16 Jitendra Wipf Group Page 16 of 20 7/22/

17 Cu Catalyzed -Phenylation of -chloramide 1a O Ph Cl + PhB(OH) 2 catalyst O base, solvent Ph 2a 25 o C Ph 3a Jitendra Mishra@ Wipf Group Page 17 of 20 7/22/

18 R 1 Cl + R 2 (HO) 2 B CuCl (10 mol%) R 3 R a 2 CO 3, THF 25 o C R 2 R 3 Jitendra Mishra@ Wipf Group Page 18 of 20 7/22/

19 Ar 1 Cl Ac + (HO) 2 B R CuCl (10 mol%) a 2 CO 3, THF 25 o C Ar 1 Ac R 3 Jitendra Mishra@ Wipf Group Page 19 of 20 7/22/

20 Conclusion -The authors utilized easily prepared and highly reactive -chloroamides to develop an efficient copper catalyzed electrophilic amination of arylboronic acids. -The developed methodoly gave high yields of diarylamides and tolerated a wide variety of functional groups, including iodo, bromo, and chloro moieties, which are usually sensitive in palladium-catalyzed reactions. -A scale up experiment was carried out to demonstrate the practicability of the method to provide biaryl amides or amines having sensitive substituents. -The availability of various boronic acids promises highlights the potential of the methodology. - Their preliminary mechanistic studies support the proposed mechanism and the results of additional investigations that are ongoing in their laboratory. Jitendra Mishra@ Wipf Group Page 20 of 20 7/22/

Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways

Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways Xiao Cheng, Charles Goodhue, and Jin-Quan Yu Brandeis University

More information

Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations

Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations Domingo Garcia-Cuadrado, Ana M. Cuadro, Bernado M. Barchin, Ana unez, Tatiana Caneque, Julio Alvarez-

More information

Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*

Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides* Pure Appl. Chem., Vol. 76, No. 3, pp. 651 656, 2004. 2004 IUPAC Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*

More information

Intramolecular Ene Reactions Utilizing Oxazolones and Enol Ethers Fisk, J.S. and Tepe, J..J J. Am. Chem. Soc., 2007, 129,

Intramolecular Ene Reactions Utilizing Oxazolones and Enol Ethers Fisk, J.S. and Tepe, J..J J. Am. Chem. Soc., 2007, 129, Intramolecular Ene Reactions Utilizing xazolones and Enol Ethers Fisk, J.S. and Tepe, J..J J. Am. Chem. Soc., 2007, 129, 3058-3059 - versus -Arylation of Aminoalcohols: rthogonal Selectivity in Copper-Based

More information

CH 3 TMG, DMF N H 3 CO 2 S. (PPh 3 ) 2 Pd 0

CH 3 TMG, DMF N H 3 CO 2 S. (PPh 3 ) 2 Pd 0 1. (a) rovide a reasonable mechanism for the following transformation. I S 2 C 3 C 3 ( 3 ) 2 2, CuI C 3 TMG, DMF 3 C 2 S TMG = Me 2 Me 2 ICu ( 3 ) 2 0 I S 2 C 3 S 2 C 3 Cu I 3 3 3 C 2 S I 3 3 3 C 2 S 3

More information

Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides

Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides Negishi Coupling of Secondary Alkylzinc alides with Aryl Bromides and Chlorides X X = Br, Cl 2 1 ZnBr 1, 2 = Alkyl Cat. Pd(OAc) 2 Ligand TF/Toluene rt or 60 o C 1 2 J. Am. Chem. Soc. 2009, ASAP Article

More information

Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.

Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis

More information

Copper-Catalyzed Reaction of Alkyl Halides with Cyclopentadienylmagnesium Reagent

Copper-Catalyzed Reaction of Alkyl Halides with Cyclopentadienylmagnesium Reagent Copper-Catalyzed eaction of Alkyl Halides with Cyclopentadienylmagnesium eagent Mg 1) cat. Cu(Tf) 2 i Pr 2, 25 o C, 3 h 2) H 2, Pt 2 Masahiro Sai, Hidenori Someya, Hideki Yorimitsu, and Koichiro shima

More information

Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans

Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans Direct xidative eck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans by Zhang,.; Ferreira, E. M.; Stoltz, B. M. Angewandte

More information

The Mechanism of Pd-Catalyzed Amination Controversy.. And Conclusion?

The Mechanism of Pd-Catalyzed Amination Controversy.. And Conclusion? The chanism of d-catalyzed Amination Controversy.. And Conclusion? R H R1 R 2 d(dba) 2 BIA, h R R1 R 2 Steve Tymonko SED Group eting 5/9/06 d-catalyzed Amination- Tin Initial Report- Kosugi, 1983 n-bu

More information

Organic Chemistry Laboratory Summer Lecture 6 Transition metal organometallic chemistry and catalysis July

Organic Chemistry Laboratory Summer Lecture 6 Transition metal organometallic chemistry and catalysis July 344 Organic Chemistry Laboratory Summer 2013 Lecture 6 Transition metal organometallic chemistry and catalysis July 30 2013 Summary of Grignard lecture Organometallic chemistry - the chemistry of compounds

More information

Microwave-promoted synthesis in water

Microwave-promoted synthesis in water Microwave-promoted synthesis in water icholas E. Leadbeater nicholas.leadbeater@uconn.edu Outline of what we do Synthesis / Methodology / ew techniques Pure organic synthesis eg. Baylis-Hillman eaction

More information

Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02

Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, 8360.

More information

Mechanistic Studies in Copper Catalysis

Mechanistic Studies in Copper Catalysis chanistic Studies in Copper Catalysis Jen Alleva May 1st 2013 Timeline of Achievements in Copper Chemistry General istorical verview first cross-couplings 1869 Ullmann Goldberg Glaser 1903 Glaser, C. Ann.

More information

Benzene and Aromatic Compounds. Chapter 15 Organic Chemistry, 8 th Edition John McMurry

Benzene and Aromatic Compounds. Chapter 15 Organic Chemistry, 8 th Edition John McMurry Benzene and Aromatic Compounds Chapter 15 Organic Chemistry, 8 th Edition John McMurry 1 Background Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Four degrees of unsaturation. It

More information

Palladium Schiff Base Complexes: Potential catalysts for C-C bond reactions

Palladium Schiff Base Complexes: Potential catalysts for C-C bond reactions Palladium Schiff Base Complexes: Potential catalysts for C-C bond reactions Moosun S. B., Bhewa, B. S., Bhowon M. G., Jhaumeer Laulloo S. * University of Mauritius, Reduit, Mauritius Email address: sabina@uom.ac.mu

More information

A Novel Approach of Using NBS as an Effective and Convenient Oxidizing Agent for Various Compounds a Survey

A Novel Approach of Using NBS as an Effective and Convenient Oxidizing Agent for Various Compounds a Survey Journal of Chemistry and Chemical Sciences, Vol.8(1), 59-65, January 2018 (An International Research Journal), www.chemistry-journal.org ISSN 2229-760X (Print) ISSN 2319-7625 (Online) A Novel Approach

More information

Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group

Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch

More information

Abstracts. p69. Keywords: C-H activation palladium catalysts arylation arenes polycyclic compounds biaryls natural products

Abstracts. p69. Keywords: C-H activation palladium catalysts arylation arenes polycyclic compounds biaryls natural products I 1.1.1 Arylation Using a Palladium(0) Catalyst F. S. Melkonyan and V. Gevorgyan p5 The palladium(0)-catalyzed C- arylation reaction is one of the pioneering transformations in C- activation chemistry

More information

Cu- Catalyzed Synthesis of Diaryl Thioethers and S- Cycles by reaction of Aryl Iodides with Carbon Disul;ide in the Presence of DBU.

Cu- Catalyzed Synthesis of Diaryl Thioethers and S- Cycles by reaction of Aryl Iodides with Carbon Disul;ide in the Presence of DBU. Cu- Catalyzed ynthesis of Diaryl Thioethers and - Cycles by reaction of Aryl odides with Carbon Disul;ide in the Presence of DBU. Peng Zhao, Hang Yin, Hongxin, Gao, Chanjuan Xi.; J. rg. Chem. ArCcle AAP

More information

Additions to Metal-Alkene and -Alkyne Complexes

Additions to Metal-Alkene and -Alkyne Complexes Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system

More information

Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo

Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo 2014.1.6 1 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook

More information

Requirements for an Effective Chiral Auxiliary Enolate Alkylation

Requirements for an Effective Chiral Auxiliary Enolate Alkylation Requirements for an Effective Chiral Auxiliary Enolate Alkylation 1. Xc must be low cost, and available in both enentiomeric forms 2. The cleavage of Xc from the substrate must occur under mild enough

More information

Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines

Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines Current Literature - May 12, 2007 Direct, Catalytic ydroaminoalkylation of Unactivated lefins with -Alkyl ylamines ' '' Ta[ 2 ] 5 (4-8 mol%), 160-165 o C 24-67h 66-95% ' '' S. B. erzon and J. F. artwig,

More information

Supporting Information. Ruthenium Catalyzed Oxidative Homocoupling of Arylboronic Acids in Water:

Supporting Information. Ruthenium Catalyzed Oxidative Homocoupling of Arylboronic Acids in Water: Supporting Information Ruthenium Catalyzed Oxidative Homocoupling of Arylboronic Acids in Water: Ligand Tuned Reactivity and Mechanistic Study Deepika Tyagi, Chinky Binnani, Rohit K. Rai, Ambikesh D. Dwivedi,

More information

both substrate : activated wastes derived from M and X one substrate : activated wastes derived from X

both substrate : activated wastes derived from M and X one substrate : activated wastes derived from X October 20th, 2007 Lit. Seminar Transition Metal Catalyzed Intermolecular ormations of - Bond : post-cross Coupling i) Cross Coupling reaction -M + '- -' (M = Zn, Sn, B,,,) ii) Direct ylation - + '- -'

More information

Palladium-Catalyzed Electrophilic Aromatic C H Fluorination

Palladium-Catalyzed Electrophilic Aromatic C H Fluorination Palladium-Catalyzed Electrophilic Aromatic C luorination +2 Pd II 2 B 4 C (5 mol %) SI (2 eq) MeC, rt 61%, 69:31 o:p C Yamamoto, K; Li, J.; Garber, J. A..; Rolfes, J. D.; Boursalian, G. B.; Borghs, J.

More information

Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid

Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,

More information

Title. Author(s)Ishiyama, Tatsuo; Itoh, Yoshiya; Kitano, Takahiro; M. CitationTetrahedron Letters, 38(19): Issue Date

Title. Author(s)Ishiyama, Tatsuo; Itoh, Yoshiya; Kitano, Takahiro; M. CitationTetrahedron Letters, 38(19): Issue Date Title Synthesis of arylboronates via the palladium(0)-cata triflates Author(s)Ishiyama, Tatsuo; Itoh, Yoshiya; Kitano, Takahiro; M CitationTetrahedron Letters, 38(19): 3447-3450 Issue Date 1997-05-12 Doc

More information

Nickel-Catalyzed Reductive Cross-Electrophile-Coupling Between Aryl and Alkyl Halides

Nickel-Catalyzed Reductive Cross-Electrophile-Coupling Between Aryl and Alkyl Halides ickel-catalyzed Reductive Cross-Electrophile-Coupling Between Aryl and Alkyl Halides Eunjae Shim Zakarian Group Literature Talk / Dec 13 th, 2018 University of California, Santa Barbara Table of Contents

More information

The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004.

The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004. The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004. Sterically Bulky Thioureas as Air and Moisture Stable Ligands for Pd-Catalyzed Heck Reactions of

More information

New Methods of Indole Formations and Applications in Total Synthesis

New Methods of Indole Formations and Applications in Total Synthesis ew Methods of Indole Formations and Applications in Total Synthesis Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles from Ethyl 3-(o-Trifluoroacetamidophenyl)-1-Propargyl Carbonate Ilaria Ambrogio,

More information

1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions

1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions 1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions 2. Copper Catalyzed One-Pot Synthesis of Multisubstituted Quinolinones Hao Wang Denmark Group Presentation

More information

Spiro Monophosphite and Monophosphoramidite Ligand Kit

Spiro Monophosphite and Monophosphoramidite Ligand Kit Spiro Monophosphite and Monophosphoramidite Ligand Kit metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials 15-5162 15-5150 15-5156 15-5163 15-5151 15-5157

More information

Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56,

Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56, Literature Report IX ynthesis of β-aminoboronates by Copper(I)- Catalyzed Addition of Diborylalkanes to Imines Reporter Checker Date : hubo Hu : Xiaoyong Zhai : 2017-9-1818 Cho,. H. et al. rg. Lett. 2016,

More information

Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College

Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic

More information

MODULE CODE: CHEM10003 ORGANIC CHEMISTRY 4 EXAM

MODULE CODE: CHEM10003 ORGANIC CHEMISTRY 4 EXAM School of Science and Sport Physical Sciences, Chemistry Paisley Campus Session 2014-15 Trimester 2 MDULE CDE: CHEM10003 RGANIC CHEMISTRY 4 EXAM Date: 15th May 2015 Time: 10.00am 12.00pm Attempt THREE

More information

FIVE MEMBERED AROMATIC HETEROCYCLES

FIVE MEMBERED AROMATIC HETEROCYCLES FIVE MEMBERED AROMATIC HETEROCYCLES 63 Electrophilic aromatic substitution reaction of five membered aromatic heterocycles X = O, S or NH a-substitution b-substitution The Substitution is regioselective

More information

Rhodium Catalyzed Alkyl C-H Insertion Reactions

Rhodium Catalyzed Alkyl C-H Insertion Reactions Rhodium Catalyzed Alkyl C-H Insertion Reactions Rh Rh Jeff Kallemeyn 5/17/05 1. Cyclopropanation The Versatile and Reactive Rhodium Carbene R + Et Rh 2 (Ac) 4 R C 2 Et N 2 2. [2,3] sigmatropic rearrangement

More information

Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions

Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions 1. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, ASAP. 2. Storer, R. L.; Carrera, D. E.;

More information

C H Activated Trifluoromethylation

C H Activated Trifluoromethylation Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation

More information

Curriculum Vitae Lingkui Meng

Curriculum Vitae Lingkui Meng Curriculum Vitae Lingkui Meng E-mail: meng.lingkui@d.mbox.nagoya-u.ac.jp Phone/Fax: 052-789-5916 Current Appointments PostDoc, MEXT Project of Integrated Research on Chemical ynthesis, Nagoya University

More information

Nucleophilic Fluorination. Souvik Rakshit Burke group Literature Seminar July 13, 2013

Nucleophilic Fluorination. Souvik Rakshit Burke group Literature Seminar July 13, 2013 Nucleophilic Fluorination Souvik Rakshit Burke group Literature Seminar July 13, 2013 Relevance 20% of pharmaceuticals contain fluorine 5-fluorouracil Antineoplastic agent, 1957 Lipitor (Atorvastatin)

More information

R 2 R 4 Ln catalyst. This manuscript describes the methods for the synthesis and application of group 4 metallocene bis(trimethylsilyl)acetylene

R 2 R 4 Ln catalyst. This manuscript describes the methods for the synthesis and application of group 4 metallocene bis(trimethylsilyl)acetylene VII Abstracts 2011 p1 2.12.15 rganometallic Complexes of Scandium, Yttrium, and the Lanthanides P. Dissanayake, D. J. Averill, and M. J. Allen This manuscript is an update to the existing Science of Synthesis

More information

Stille-type cross coupling reactions with tetraalkynyl stannanes

Stille-type cross coupling reactions with tetraalkynyl stannanes Stille-type cross coupling reactions with tetraalkynyl stannanes Andrey S. Levashov,* Dmitriy S. Buriy, Valeriy V. Konshin and Alexey A. Andreev (deceased) Kuban State University, 149 Stavropolskaya Str.,

More information

Suggested solutions for Chapter 40

Suggested solutions for Chapter 40 s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig

More information

Palladium-Catalyzed Oxygenation of Unactivated sp 3 C-H Bonds

Palladium-Catalyzed Oxygenation of Unactivated sp 3 C-H Bonds Palladium-Catalyzed xygenation of Unactivated sp 3 C- Bonds Pd(Ac) 2 5 mol% PhI(Ac) 2 1.1 eq. Pd 2 Ac Desai, L. P.; ull, K. L.; Sanford *, M. S. University of Michigan J. Am. Chem. Soc. 2004, 126, ASAP

More information

Sonogashira: in situ, metal assisted deprotonation

Sonogashira: in situ, metal assisted deprotonation M.C. White, Chem 253 Cross-Coupling -120- Week of ctober 11, 2004 Sonogashira: in situ, metal assisted deprotonation catalytic cycle: ' (h 3 ) n d II The first report: h Sonogashira T 1975 (50) 4467. h

More information

Synthesis and Structure of Alcohols Alcohols can be considered organic analogues of water.

Synthesis and Structure of Alcohols Alcohols can be considered organic analogues of water. Synthesis and Structure of Alcohols Alcohols can be considered organic analogues of water. Alcohols are usually classified as primary, secondary and tertiary. Alcohols with the hydroxyl bound directly

More information

2016 Pearson Education, Inc. Isolated and Conjugated Dienes

2016 Pearson Education, Inc. Isolated and Conjugated Dienes 2016 Pearson Education, Inc. Isolated and Conjugated Dienes 2016 Pearson Education, Inc. Reactions of Isolated Dienes 2016 Pearson Education, Inc. The Mechanism Double Bonds can have Different Reactivities

More information

Chapter 21. Organic Chemistry 4 th Edition Paula Yurkanis Bruice. More About Amines. Heterocyclic Compounds

Chapter 21. Organic Chemistry 4 th Edition Paula Yurkanis Bruice. More About Amines. Heterocyclic Compounds Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 21 More About Amines. Heterocyclic Compounds Irene Lee Case Western Reserve University Cleveland, OH 2004, Prentice Hall Amines An amine is

More information

Direct Catalytic Cross-Coupling of Organolithium

Direct Catalytic Cross-Coupling of Organolithium Literature report Direct Catalytic Cross-Coupling of Organolithium Compounds Reporter: Zhang-Pei Chen Checker: Mu-Wang Chen Date: 02/07/2013 Feringa, B.L.et al. Feringa, B. L. et al. Nature Chem. 2013,

More information

Palladium-Catalyzed Alkylarylation of Acrylamides with

Palladium-Catalyzed Alkylarylation of Acrylamides with Supporting Information Palladium-Catalyzed Alkylarylation of Acrylamides with Unactivated Alkyl Halides Hua Wang, Li-a Guo, and Xin-Hua Duan* Department of Chemistry, School of Science and ME Key Laboratory

More information

BENZENE & AROMATIC COMPOUNDS

BENZENE & AROMATIC COMPOUNDS BENZENE & AROMATIC COMPOUNDS Dr. Zainab M Almarhoon 2 Learning Objectives By the end of chapter four the students will: Understand the resonance description of structure of benzene Understand the hybridization

More information

Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014

Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014 Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation:

More information

Chapter 5 N S. Typical Reactivity of Pyridines, Quinolines and Isoquinolines

Chapter 5 N S. Typical Reactivity of Pyridines, Quinolines and Isoquinolines Chapter 5 S Typical Reactivity of Pyridines, Quinolines and Isoquinolines 1 2 Typical Reactivity of Pyridines pyridines are much less susceptible to electrophilic substitution than benzene and much more

More information

Transition-metal catalyzed C C bond cleavage

Transition-metal catalyzed C C bond cleavage Transition-metal catalyzed C C bond cleavage 2011.09.17 Chaoren Shen Wanbin Group Literature Seminar 1.Decarboxylation(Cu Ag Pd Rh) 2. Decarbonylation(i Pd) 3. Deacylation(Pd Rh) Jon A. Tunge( University

More information

o-palladated cat. [Chem. Comm (1999)] [Org. Lett. 2, 1826 (2000)] [Org. Lett. 2, 2881 (2000)] [JACS 41, 9550 (1999)]

o-palladated cat. [Chem. Comm (1999)] [Org. Lett. 2, 1826 (2000)] [Org. Lett. 2, 2881 (2000)] [JACS 41, 9550 (1999)] 3. Boron -- eview [Suzuki Chem. ev. 95, 2457 (1995)] U77b ydroboration also attractive but B Pd transmetallation difficult - must produce stable B product - solved (by Suzuki) by adding base to make Borates

More information

ORGANIC - BROWN 8E CH. 22- REACTIONS OF BENZENE AND ITS DERIVATIVES

ORGANIC - BROWN 8E CH. 22- REACTIONS OF BENZENE AND ITS DERIVATIVES !! www.clutchprep.com CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION GENERAL MECHANISM Benzene reacts with very few reagents. It DOES NOT undergo typical addition reactions. Why? If we can get benzene to

More information

11/26/ Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds

11/26/ Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds 9.5 Polycyclic Aromatic Compounds The general concept of aromaticity can be extended to include polycyclic aromatic compounds Benzo[a]pyrene is one of the cancer-causing substances found in tobacco smoke

More information

Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics

Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters.

More information

Ch 22 Carbonyl Alpha ( ) Substitution

Ch 22 Carbonyl Alpha ( ) Substitution Ch 22 Carbonyl Alpha () Substitution The overall reaction replaces an H with an E + The acid-catalyzed reaction has an enol intermediate The base-catalyzed reaction has an enolate intermediate Keto-Enol

More information

Fundamentals of Organic Chemistry

Fundamentals of Organic Chemistry Fundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1) King Saud University College of Science, Chemistry Department CHEM 109 CHAPTER 3. AROMATIC HYDROCARBONS Aromatic

More information

Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines

Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert- Butanesulfinyl Aldimines R BR 2 J. Am. Chem. Soc. 2008, 130, 6910. Melissa A. Beenen, Chihul An, and Jonathan A. Ellman rrent

More information

Benzenes & Aromatic Compounds

Benzenes & Aromatic Compounds Benzenes & Aromatic Compounds 1 Structure of Benzene H H C C C H C 6 H 6 H C C C H H A cyclic conjugate molecule Benzene is a colourless odourless liquid, boiling at 80 o C and melting at 5 o C. It is

More information

Denmark Group Meeting. & Electrophilic rearrangement of amides

Denmark Group Meeting. & Electrophilic rearrangement of amides Denmark Group Meeting Palladium catalyzed Dearomatizationeaction & Electrophilic rearrangement of amides 11 th Bo Peng th Feb. 2014 1 https://maps.google.com 2 Palladium catalyzed Dearomatization eaction

More information

11/30/ Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions

11/30/ Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions Chapter 9 Problems: 9.1-29, 32-34, 36-37, 39-45, 48-56, 58-59, 61-69, 71-72. 9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic

More information

Electrophilic Carbenes

Electrophilic Carbenes Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)

More information

Chapter 8 Alkenes: Reactions

Chapter 8 Alkenes: Reactions Chamras Glendale Community College Organic Chemistry 105 Chapter 8 Alkenes: Reactions Name Type 1. alo-hydrogenation (Ionic & Radical) Electrophilic Addition 2. ydration (Acid-Catalyzed) Electrophilic

More information

Section Practice Exam II Solutions

Section Practice Exam II Solutions Paul Bracher Chem 30 Section 7 Section Practice Exam II s Whether problems old r problems new, You d better practice, r you ll fail exam II. -- Anonymous TF Problem 1 a) Rank the following series of electrophiles

More information

Alkyl phenyl ketones are usually named by adding the acyl group as prefix to phenone.

Alkyl phenyl ketones are usually named by adding the acyl group as prefix to phenone. Aldehydes, Ketones and Carboxylic Acids Nomenclature of aldehydes and ketones Aldehydes: Often called by their common names instead of IUPAC names. Ketones: Derived by naming two alkyl or aryl groups bonded

More information

Transition Metal-Catalyzed 1,2-Diamination of Alkenes. Group Meeting Timothy Chang

Transition Metal-Catalyzed 1,2-Diamination of Alkenes. Group Meeting Timothy Chang Transition Metal-Catalyzed 1,2-Diamination of Alkenes Group Meeting Timothy Chang 04-27-10 Valuable 1,2-Diamine Motif H H S Biotin CH H H Pt Eloxatin (Anticaner) H 2 AcH CHEt 2 Tamiflu (Antiviral) Et Ph

More information

Rachel Whittaker Dong Group Literature Talk October 10, Ref: Perez-Temprano, M.H, Casares, J.A., Espinet, P., Chem. Eur. J. 2012, 18, 1864.

Rachel Whittaker Dong Group Literature Talk October 10, Ref: Perez-Temprano, M.H, Casares, J.A., Espinet, P., Chem. Eur. J. 2012, 18, 1864. Rachel Whittaker Dong Group Literature Talk October 10, 2013 Ref: Perez-Temprano, M.H, Casares, J.A., Espinet, P., Chem. Eur. J. 2012, 18, 1864. Overview Introduction Group Exchange C-C Bond Forming Reactions

More information

AROMATIC & HETEROCYCLIC CHEMISTRY

AROMATIC & HETEROCYCLIC CHEMISTRY - 1 - AROMATIC & HETEROCYCLIC CHEMISTRY Aromatic Chemistry Aromaticity This confers an energetic stability over the equivalent double bond system. This can be explained from an MO point of view. The Huckel

More information

Functional Groups. Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity.

Functional Groups. Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity. Functional Groups Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity. Organic halides: a hydrogen is replaced by a halogen fluoro-,

More information

Organic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall

Organic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall Organic Chemistry, 7 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds 2010, Prentice Hall Electrophilic Aromatic Substitution Although h benzene s pi electrons are in a stable aromatic

More information

Iron in the Service of Chromium: The ortho-benzannulation of trans,trans-dienyl Fischer Carbene Complexes

Iron in the Service of Chromium: The ortho-benzannulation of trans,trans-dienyl Fischer Carbene Complexes Iron in the Service of Chromium: The ortho-benzannulation of trans,trans-dienyl Fischer Carbene Complexes Yiqian Lian and William D. Wulff (Michigan State University) JACS 2005, 127, 17162-17163. Markus

More information

There is basically one simple mechanism for all electrophilic aromatic substitutions:

There is basically one simple mechanism for all electrophilic aromatic substitutions: Substitution Reactions of Aromatic Compounds Simple alkenes tend to undergo addition reactions: The elements of the reagent (HBr or Br2) are simply added to the starting material. This is called, unsurprisingly,

More information

Air-stable phosphine oxides as preligands for catalytic activation reactions of C Cl, C F, and C H bonds*

Air-stable phosphine oxides as preligands for catalytic activation reactions of C Cl, C F, and C H bonds* Pure Appl. Chem., Vol. 78, No. 2, pp. 209 214, 2006. doi:10.1351/pac200678020209 2006 IUPAC Air-stable phosphine oxides as preligands for catalytic activation reactions of C Cl, C F, and C H bonds* Lutz

More information

Heterocyclic Chemistry Midterm Examination. 3 May Professor Baran Department of Chemistry The Scripps Research Institute

Heterocyclic Chemistry Midterm Examination. 3 May Professor Baran Department of Chemistry The Scripps Research Institute eterocyclic Chemistry Midterm Examination 3 May 2013 Professor Baran Department of Chemistry The cripps Research Institute ame: Last 4 digits of your ocial ecurity #: This is a 2-hour test that you have

More information

Aromatic Compounds II

Aromatic Compounds II 2302272 Org Chem II Part I Lecture 2 Aromatic Compounds II Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 17 in Organic Chemistry, 8 th Edition, L.

More information

CHO. OMe. endo. xylene, 140 o C, 2 h 70% 1. CH 2 (OMe) 2, MeOH TsOH, rt 2. Bu 2 O, 1,2-dichloroethane 140 o C, 2 h 3. 6 M HCl, THF, rt 44%

CHO. OMe. endo. xylene, 140 o C, 2 h 70% 1. CH 2 (OMe) 2, MeOH TsOH, rt 2. Bu 2 O, 1,2-dichloroethane 140 o C, 2 h 3. 6 M HCl, THF, rt 44% VII Abstracts 2010 p1 2.4.12 Arene rganometallic Complexes of Chromium, Molybdenum, and Tungsten M. Uemura This review is an update to Section 2.4 and covers the literature from 1999 to 2010. (h 6 -Arene)chromium

More information

12/27/2010. Chapter 15 Reactions of Aromatic Compounds

12/27/2010. Chapter 15 Reactions of Aromatic Compounds Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen atom

More information

Chapter 15 Reactions of Aromatic Compounds

Chapter 15 Reactions of Aromatic Compounds Chapter 15 1 Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen

More information

Total Syntheses of Minfiensine

Total Syntheses of Minfiensine Total Syntheses of Minfiensine Douany, A. B.; umphreys, P. G.; verman, L. E.*; Wrobelski, A. D., J. Am. Chem. Soc. 2008, ASAP. D: 10.1021/ja800163v Shen, L.; Zhang, M.; Wu, Y.; Qin, Y.*, Angew. Chem. nt.

More information

Investigation of the Role and Form. Formation. Michael Enright

Investigation of the Role and Form. Formation. Michael Enright Investigation of the Role and Form of Silver Catalysts in C N Bond Formation Michael Enright Ripon College Importance Carbon Nitrogen Bonds Medicine Biological compounds Make C N bonds whenever we want

More information

Recent Developments in Alkynylation

Recent Developments in Alkynylation --New approaches to introduce an alkynyl group Reporter: Zhao-feng Wang Supervisor: Yong Huang 2013-03-27 Contents 1. Introduction of Acetylene Chemistry 2. Nucleophilic alkynylation : Classic text book

More information

Recent Advances in C-B Bond Formation through a Free Radical Pathway

Recent Advances in C-B Bond Formation through a Free Radical Pathway Recent Advances in C-B Bond Formation through a Free Radical Pathway G. Yan. D. Huang, X. Wu, Adv. Synth. Catal. 2017, 359, 188. Daniel Meyer University of Bern 18.01.2018, Topic Review Classical Methodes

More information

Reducing Agents. Linda M. Sweeting 1998

Reducing Agents. Linda M. Sweeting 1998 Reducing Agents Linda M. Sweeting 1998 Reduction is defined in chemistry as loss of oxygen, gain of hydrogen or gain of electrons; the gain of electrons enables you to calculate an oxidation state. Hydride

More information

R 4. metathesis. reductive elimination

R 4. metathesis. reductive elimination VII Abstracts 2011 p1 2.10.18 rganometallic Complexes of Titanium T. Takeda and A. Tsubouchi This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the preparation

More information

Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2009, 131, Daniel Tzvi Cohen Short Literature Feb. 23, MeO HO OH. COOH ( )-Plicatic Acid OH OH

Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2009, 131, Daniel Tzvi Cohen Short Literature Feb. 23, MeO HO OH. COOH ( )-Plicatic Acid OH OH Asymmetric Total Synthesis of ( )-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstituted lefins H H H H CH ( )-Plicatic Acid H H Sun, B.F.;

More information

Stable gold(iii) catalysts by oxidative addition of a carboncarbon

Stable gold(iii) catalysts by oxidative addition of a carboncarbon Stable gold(iii) catalysts by oxidative addition of a carboncarbon bond Chung-Yeh Wu, Takahiro oribe, Christian Borch Jacobsen & F. Dean Toste ature, 517, 449-454 (2015) presented by Ian Crouch Literature

More information

8. Methods in Developing Mobile Phase Condition for C18 Column

8. Methods in Developing Mobile Phase Condition for C18 Column I. HPLC Columns Technical Information 8. Methods in Developing Mobile Phase Condition for C18 Column Introduction In reversed phase HPLC, octadecyl group bonded silica columns (C18, ODS) are the most widely

More information

Class XII: Chemistry Chapter 13: Amines Top concepts

Class XII: Chemistry Chapter 13: Amines Top concepts Class XII: Chemistry Chapter 13: Amines Top concepts 1. Amines are regarded as derivatives of ammonia in which one, two or all three hydrogen atoms are replaced by alkyl or aryl group 2. Classification

More information

Chem 1075 Chapter 19 Organic Chemistry Lecture Outline

Chem 1075 Chapter 19 Organic Chemistry Lecture Outline Chem 1075 Chapter 19 Organic Chemistry Lecture Outline Slide 2 Introduction Organic chemistry is the study of and its compounds. The major sources of carbon are the fossil fuels: petroleum, natural gas,

More information

Chemistry of Benzene: Electrophilic Aromatic Substitution

Chemistry of Benzene: Electrophilic Aromatic Substitution Chemistry of Benzene: Electrophilic Aromatic Substitution Why this Chapter? Continuation of coverage of aromatic compounds in preceding chapter focus shift to understanding reactions Examine relationship

More information

Chem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below.

Chem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below. hem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below. TP l Et step 8 4 5 eagents used in synthesis A B D E F a DMF (solvent) 1. (i-pr) 2 Li (LDA)/TF

More information

Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternary α-amino Acid Derivatives

Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternary α-amino Acid Derivatives Direct rganocatalytic Enantioselective Mannich eactions of Ketimines: An Approach to ptically Active Quaternary α-amino Acid Derivatives Wei Zhang, Steen Saaby, and Karl Anker Jorgensen The Danish ational

More information

Hydrocarbons and their Functional Groups

Hydrocarbons and their Functional Groups Hydrocarbons and their Functional Groups Organic chemistry is the study of compounds in which carbon is the principal element. carbon atoms form four bonds long chains, rings, spheres, sheets, and tubes

More information

Electronegativity Scale F > O > Cl, N > Br > C, H

Electronegativity Scale F > O > Cl, N > Br > C, H Organic Chem Chapter 12 Alkanes Organic chemistry is the study of carbon compounds. Carbon has several properties that are worth discussing: Tetravalent Always forms 4 bonds Can form multiple bonds (double

More information