Modern Synthetic Methods
|
|
|
- Tracey Neal
- 5 years ago
- Views:
Transcription
1 Modern Synthetic Methods Dr. Dorian Didier
2 Functionnalized Organometallic Reagents C-N, C-O and C-S Bond Formation Introduction to Organoboron Chemistry Introduction to Organosilicon Chemistry Carbometallation Reactions
3 Functionnalized Organometallic Reagents C-N, C-O and C-S Bond Formation Introduction to Organoboron Chemistry Introduction to Organosilicon Chemistry Carbometallation Reactions
4 Generalities Suzuki-Miyaura with R-BF 3 K Reagents Stille Negishi Corriu-Kumada-Tamao Sonogashira Heck Arylation of Enolates
5 Generalities 4
6 Generalities I >> Br > OTf > Cl Very slow Slow Fast Fast Very slow 5
7 Suzuki-Miyaura High tolerance of functionnal grougs T. Heh et al. Tetrahedron Lett. 2005, 46,
8 Suzuki-Miyaura A. E. Thompson et al. J. Org. Chem. 2005, 70, 388. M. Uesugi et al. J. Am. Chem. Soc. 2009, 131,
9 Suzuki-Miyaura C. M. Crudden et al. J. Am. Chem. Soc. 2009, 131, Works with hindered substrates S. L. Buchwald et al. J. Am. Chem. Soc. 2005, 127,
10 Suzuki-Miyaura Iterative M. D. Burke et al. J. Am. Chem. Soc. 2007, 129, J. Am. Chem. Soc. 2009, 131,
11 Suzuki-Miyaura Iterative M. Suginome et al. J. Am. Chem. Soc. 2007, 129, 758. Org. Lett. 2008, 10, 377. Org. Lett. 2009, 11, 1899.
12 Suzuki-Miyaura Better Understanding of the Mechanism 11
13 Suzuki-Miyaura Better Understanding of the Mechanism Oxidative Addition Csp 3 -X usually slow Favoured by Electronically Rich Ligands Bulky Ligands Can lead to b-h elimination
14 Suzuki-Miyaura Better Understanding of the Mechanism G. A. Molander Angew. Chem. Int. Ed. 2009, 48, J. A. Soderquist J. Org. Chem. 1998, 63, 461. Y. Kishi J. Am. Chem. Soc. 1987, 109, TM is accelerated by a base 13
15 Suzuki-Miyaura Better Understanding of the Mechanism Avoiding b-h Elimination Bulky Ligands Chelating Ligands 14
16 with R-BF 3 K Reagents G. Molander et al. J. Org. Chem. 2005, 70, G. Molander et al. J. Org. Chem. 2002, 67,
17 with R-BF 3 K Reagents G. A. Molander et al. J. Am. Chem. Soc. 2008, 130, G. A. Molander et al. J. Org. Chem. 2008, 73, 7481
18 with R-BF 3 K Reagents Mechanism G. A. Molander et al. J. Am. Chem. Soc. 2010, 132,
19 Overview of Different (pre)catalytic Systems and Common Ligands 17
20 Stille On the Mechanism P. Espinet et al. J. Am. Chem. Soc. 1998, 120, J. Am. Chem. Soc. 2000, 122, J. F. Hartwig et al. J. Am. Chem. Soc. 2001, 123, G.C. Fu et al. Angew. Chem. Int. Ed. 1999, 38, G.C. Fu et al. J. Am Chem. Soc. 2003, 125,
21 Stille E. J. Corey et al. J. Am. Chem. Soc. 1999, 121, G. Guillaumet et al. Org. Lett. 2003, 5, 803. L. S. Liebeskind et al. Org. Lett. 2003, 5,
22 Negishi High Tolerance of Functionnal Groups P. Knochel et al. Org. Lett. 2005, 7,
23 Negishi «Quinoxaline» S. L. Buchwald et al. J. Am. Chem. Soc. 2004, 126, G. C. Fu et al. J. Am. Chem. Soc. 2001, 123,
24 Negishi Alkenyl-Zinc G. C. Fu et al. J. Am. Chem. Soc. 2001, 123, J. Am. Chem. Soc. 2002, 124, Alkyl-Zinc M. G. Organ et al. J. Org. Chem. 2005, 70, Org. Lett. 2005, 7,
25 Negishi Alkynyl-Zinc E. Negishi et al. Org. Lett 2003, 5, J. A. Miller et al. Tetrahedron Lett. 2004, 45, Tetrahedron Lett. 2005, 46, Org. Lett 2001, 3, (benzylic electrophiles) (aryl electrophiles) 23
26 Negishi Compatibility P. Knochel et al. Org. Lett. 2008, 10, P. Knochel et al. Chem. Eur. J. 2009,15,
27 Corriu-Kumada-Tamao S. Buchwald et al. J. Am. Chem. Soc. 2007, 129,
28 Corriu-Kumada-Tamao Ph-MgBr With -Cl and -F W. A. Herrmann et al. Angew. Chem. Int. Ed. 2000, 39, E. Nakamura et al. J. Am. Chem. Soc. 2005, 127,
29 Corriu-Kumada-Tamao Preparation Acceleration Effect Same observation in the presence of : P. Knochel Angew. Chem. Int. Ed. 2009, 48,
30 Corriu-Kumada-Tamao 28
31 Corriu-Kumada-Tamao 29
32 Corriu-Kumada-Tamao Mechanism? Radicals? 30
33 Corriu-Kumada-Tamao Initiation Propagation 31
34 Corriu-Kumada-Tamao Variation of Electrophiles J. A. Miller et al. Tetrahedron Lett. 2001, 42, J. W. Dankwardt Angew. Chem. Int. Ed. 2004, 43, V. Snieckus et al. Angew. Chem. Int. Ed. 2004, 43,
35 Corriu-Kumada-Tamao Copper-Catalyzed CKT Cross-Coupling N. Kambe et al. Angew. Chem. Int. Ed. 2007, 46,
36 Corriu-Kumada-Tamao Copper-Catalyzed CKT Cross-Coupling MgCl MgCl N. Kambe et al. Angew. Chem. Int. Ed. 2007, 46,
37 Corriu-Kumada-Tamao Copper-Catalyzed CKT Cross-Coupling N. Kambe et al. Angew. Chem. Int. Ed. 2007, 46,
38 Corriu-Kumada-Tamao Copper-Catalyzed CKT Cross-Coupling N. Kambe et al. Angew. Chem. Int. Ed. 2007, 46,
39 Corriu-Kumada-Tamao Manganese-Catalyzed CKT Cross-Coupling Stereoretention G. Cahiez et al. Org. Lett. 2008, 10,
40 Corriu-Kumada-Tamao Silver-Catalyzed CKT Cross-Coupling Specially on Bulky Electrophiles K. Oshima Org. Lett. 2008, 10,
41 Corriu-Kumada-Tamao Special Case of N-tosylhydrazones P. Aznar et al. Angew. Chem. Int. Ed. 2007, 46,
42 Corriu-Kumada-Tamao Special Case of N-tosylhydrazones 40
43 Corriu-Kumada-Tamao Special Case of N-tosylhydrazones 41
44 Sonogashira From terminal alkynes Can be catalyzed by few transition metal complexes 42
45 Sonogashira 43
46 Sonogashira S. L. Buchwald et al. Org.Lett. 2000, 2, C.-G. Cho et al. Org. Lett. 2002, 4,
47 Sonogashira Copper-Catalyzed, Paladium-Free M. Taillefer et al. Org. Lett. 2008, 10,
48 Sonogashira M. Taillefer et al. Org. Lett. 2008, 10,
49 Sonogashira Iron-Catalyzed M. Nakamura et al. Angew. Chem. Int. Ed. 2011, 50,
50 Heck 48
51 Heck G. C. Fu et al. J. Org. Chem. 1999, 64, 10. I. Beletskaya et al. Chem. Rev. 2000, 100, (review) 49
52 Heck S. Cacchi et al. Org. Lett. 2003, 5, 777. T. Tu et al. Synlett, 2011,
53 Heck M. Santelli et al. Synthesis 2008, T. Skydstrup et al. Angew. Chem. Int. Ed. 2006, 45,
54 Heck M. Santelli, Synthesis, 2006, 3495 J. Xiao, Angew. Chem. Int. Ed., 2006, 45,
55 Heck regioselectivities? 53
56 Heck J. Zhou et al. J. Am. Chem. Soc. 2014, 136,
57 Heck Decarboxylative Heck A. G. Myers et al. J. Am. Chem. Soc. 2002, 124,
58 Heck Decarboxylative Heck A. G. Myers et al. Org. Lett. 2004, 6,
59 Arylation of Enolates 57
60 Arylation of Enolates J. F. Hartwig et al. J. Org. Chem. 1998, 63, Lloyd-Jones et al. Angew. Chem. Int. Ed. 2002, 41,
61 Arylation of Enolates S. L. Buchwald et al. J. Am. Chem. Soc. 2000, 122, J. F. Hartwig et al.j. Am. Chem. Soc. 2002, 124, S. L. Buchwald et al. J. Org. Chem. 2002, 67,
62 Arylation of Enolates J. F. Hartwig et al. J. Am. Chem. Soc. 2005, 127,
63 Arylation of Enolates F. Y. Kwong et al. Org. Lett. 2007, 9,
64 Arylation of Enolates Remote Arylation J. F. Hartwig et al. Angew. Chem. Int. Ed. 2010, 49, P. Knochel et al. Org. Lett. 2011, 13,
Iron Catalysed Coupling Reactions
LONG LITERATURE REPORT Iron Catalysed Coupling Reactions Mingyu Liu 2017. 8. 31 1 Fe [Ar]3d 6 4s 2 The fourth most common element in the Earth s crust Relatively less understanding and manipulation of
Asymmetric Palladium Catalyzed Cross-Coupling Reactions. Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1
Asymmetric Palladium Catalyzed Cross-Coupling Reactions Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1 Palladium Catalyzed Cross-Coupling Reactions 2 Kumada/Negishi Cross-Coupling Kumada:
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
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
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
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015 New strategies in organic synthesis nsf-cchf.com What
Ligand Effects in Nickel Catalysis. Anthony S. Grillo Chem 535 Seminar October 22, 2012
Ligand in Nickel Catalysis Anthony S. Grillo Chem 535 Seminar October 22, 2012 Transition Metals in Chemistry Organotransition Metal Chemistry, Hartwig, J. F. University Science Books: Mill Valley, CA,
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
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
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
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,
Iron Catalyzed Cross Coupling: Mechanism and Application. Matthew Burk Denmark Group Meeting
Iron Catalyzed Cross Coupling: Mechanism and Application Matthew Burk Denmark Group Meeting 3-10-2009 Long Induction Period: Early History Of Iron Catalyzed Cross Coupling 1941: Effect of metal impurities
Functionalized Organometallic Reagents
Availability Availability Preparation via Insertion Grignard s Synthesis Generally Considered as a Radical Process Schlenk Equilibrium Parasite Reactions Reversible Reaction in THF Substitution Reactions
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation
Enantioselective Borylations. David Kornfilt Denmark Group Meeting Sept. 14 th 2010
Enantioselective Borylations David Kornfilt Denmark Group Meeting Sept. 14 th 2010 30.000-foot View Enantioenriched Organoboranes What to do with them Crudden C. M. et. al., Eur. J. Org. Chem. 2003, 46
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:
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)
Coupling Reactions with Alkyl Halides. Lizzie O Bryan Literature Seminar January 31, 2008
Recent Advances in Nickel Catalyzed Cross Coupling Reactions with Alkyl Halides Lizzie Bryan Literature Seminar January 31, 2008 Transitions Metal Catalyzed Cross Coupling Reactions Extensively used for
Organocopper Reagents
rganocopper eagents General Information!!! why organocopper reagents? - Efficient method of C-C bond formation - Cu less electropositive than Li or Mg, so -Cu bond less polarized - consequences: 1. how
Advanced Organic Chemistry
D. A. Evans, G. Lalic Chem 530A Chemistry 530A Advanced Organic Chemistry Lecture notes part 8 Carbanions Organolithium and Grignard reagents Organocopper reagents 1. Direct metalation 2. From radical
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,
A Simple Introduction of the Mizoroki-Heck Reaction
A Simple Introduction of the Mizoroki-Heck Reaction Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2016/2/3 Content Introduction Intermolecular Mizoroki-Heck Reaction Intramolecular Mizoroki-Heck
Metalloporphyrin. ~as efficient Lewis acid catalysts with a unique reaction-field~ and. ~Synthetic study toward complex metalloporphyrins~
Metalloporphyrin ~as efficient Lewis acid catalysts with a unique reaction-field~ and ~Synthetic study toward complex metalloporphyrins~ Literature Seminar Kenta Saito (D1) 1 Topics Chapter 1 ~as efficient
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations. Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date:
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date: 2013-04-08 0 Content Introduction C-H Oxidation Initiated by Single-Electron Transfer(SET)
Self-stable Electrophilic Reagents for Trifluoromethylthiolation. Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date:
Self-stable Electrophilic Reagents for Trifluoromethylthiolation Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date: 2017-12-25 Content Introduction Trifluoromethanesulfenates: Preparation and reactivity
Title. Author(s)Miyaura, Norio. CitationJournal of Organometallic Chemistry, 653(1-2): Issue Date Doc URL. Type.
Title Cross-coupling reaction of organoboron compounds via Author(s)Miyaura, Norio CitationJournal of Organometallic Chemistry, 653(1-2): 54-57 Issue Date 2002-07-01 Doc URL http://hdl.handle.net/2115/15835
COUPLING OF 2-ARYL-4-CHLORO-3-IODOQUINOLINE DERIVATIVES WITH TERMINAL
Student number: 45878382 I declare that REGIOSELECTIVITY OF PALLADIUM-CATALYZED SONOGASHIRA CROSS- COUPLING OF 2-ARYL-4-CHLORO-3-IODOQUINOLINE DERIVATIVES WITH TERMINAL ALKYNES is my own work and that
CHEM 251 (4 credits): Description
CHEM 251 (4 credits): Intermediate Reactions of Nucleophiles and Electrophiles (Reactivity 2) Description: An understanding of chemical reactivity, initiated in Reactivity 1, is further developed based
Functionalized main-group organometallics for organic synthesis*
Pure Appl. Chem., Vol. 74, No. 1, pp. 11 17, 2002. 2002 IUPAC Functionalized main-group organometallics for organic synthesis* Paul Knochel, Eike Hupe, Wolfgang Dohle, David M. Lindsay, Véronique Bonnet,
Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic - Chloroamides
Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic - Chloroamides The MIT Faculty has made this article openly available. Please share how this access benefits
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
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,
Dual Role of Silanol Groups in Cyclopropanation and Hiyama-Denmark Cross-Coupling Reactions
Dual Role of Silanol Groups in Cyclopropanation and Hiyama-Denmark Cross-Coupling Reactions L.-P. B. Beaulieu, L. B. Delvos, A. B. Charette* Département de Chimie, Université de Montréal, P.O. Box. 6138,
Functionalization of C O Bonds. Stefan McCarver. MacMillan Lab Group Meeting
Functionalization of C Bonds Stefan McCarver MacMillan Lab Group eting November 23 rd, 2016 Functionalization of C Bonds "X" X homolytic cleavage catalyst M oxidative addition Why is C Bond Manipulation
On the Role of Metal Contaminants in Catalyses with FeCl
On the Role of Metal Contaminants in Catalyses with FeCl The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation As Published Publisher
Beyond Directing Groups
Beyond Directing Groups Transition-Metal-Catalyzed C-H Activation of Simple Arenes Reporter: Huan Sun Supervisor: Yong Huang 2013-01-07 N. Kuhl, M. N. Hopkinson, J. W. Delord, F. Glorius, Angew. Chem.
A Stille or Suzuki reaction is a good choice for this coupling O O because they are functional group tolerant, no radical chemistry F
Chemistry 253 roblem et 3 Due: Friday, ctober 15th ame TF 1. For the following products of cross coupling reactions and indicated bond disconnections, please indicate a reasonable cross coupling protocol
Hybridization of Nickel Catalysis and Photoredox Catalysis. Literature seminar#1 B4 Hiromu Fuse 2017/02/04(Sat)
Hybridization of Nickel Catalysis and Photoredox Catalysis Literature seminar#1 B4 Hiromu Fuse 2017/02/04(Sat) Introduction Novel cross coupling was reported! Highly selective sp 3 C-H functionalization!
Oxidative couplings of two nucleophiles
Oxidative Couplings of Hydrocarbons Oxidative couplings of two nucleophiles Oxidants involved: O 2 H 2 O 2 high h valent metals(copper salts) halides(iodine(Ⅲ) oxidants) Lei, A. W. Chem. Rev., 2011, 111,
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
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
Mechanistic Insides into Nickamine-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions
Mechanistic Insides into Nickamine-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions Abstract Within the last decades the transition metal-catalyzed cross-coupling of non-activated alkyl halides has significantly
Tautomerism and Keto Enol Equilibrium
Tautomerism and Keto Enol Equilibrium Enols & enolates are important nucleophiles in organic & biochemistry. Keto-Enol Equilibrium: Tautomerisation can be catalyzed by either acids or bases. Relative stability
Zr-Catalyzed Carbometallation
-Catalyzed Carbometallation C C C C ML n C C ML n ML n C C C C ML n ML n C C ML n Wipf Group esearch Topic Seminar Juan Arredondo November 13, 2004 Juan Arredondo @ Wipf Group 1 11/14/2004 Carbometallation
CHEM 344 Organometallic Chemistry Practice Problems (not for credit)
CHEM 344 Organometallic Chemistry Practice Problems (not for credit) Name (print): TA name (print): 1) Careful choice of solvent is essential for the successful generation and reaction of a Grignard reagent.
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity Reporter: Cong Liu Checker: Hong-Qiang Shen Date: 2017/02/27
Direct α-arylation of Ketones
Direct α-arylation of Ketones Zhensheng Ding January 29, 2003 Department of Chemistry Michigan State University Direct α-arylation of Ketone Outline Introduction Mechanistic Study Factors Influencing the
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
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
Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes
Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation As Published
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/ *&%&*,$.&-!"!3$!4$!5)01+!.*!06'2
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/012 546*&%&*,$.&-!"!3$!4$!5)01+!.*!06'2 C-C Bond Formation: Cross-coupling Reaction of rganometal Compounds with rganic alids M C-m + X-C C-C
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
Review. Recent Developments in Pd-catalyzed Carbonylation Reaction. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang
Review Recent Developments in Pd-catalyzed Carbonylation Reaction Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang History 1962, E. Fischer Z. Nafurforsch. 1962, 17b, 484. 1963, R. Heck J. Org.
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
Boron containing 1,1-Dimetallicalkane Reagents
Boron containing 1,1-Dimetallicalkane Reagents Topic Talk Xun Liu July 25, 2013 Outline 1. 1,1-Borio-lithioalkane reagents 2. 1,1-Boronalkane reagents 3. 1,1-Borio-zincioalkane Reagents and 1,1-Borio-cuprioalkane
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
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
Manganese-Catalyzed Late- Stage Aliphatic C H Azidation
Wipf group current literature Manganese-Catalyzed Late- Stage Aliphatic C H Azidation J. Am. Chem. Soc. 2015, 137, 5300 5303 Xiongyi Huang, Tova M. Bergsten, and John T. Groves Department of Chemistry,
Xuefeng Jiang Professor Education Academic Career Awards International Invited Lecture USA Germany Shanghai Taiwan Singapore)
Xuefeng Jiang( 姜雪峰 ) Professor East China Normal University, 200062, Shanghai, China Tel: +86-21-52133654 E-mail: xfjiang@chem.ecnu.edu.cn Web: http://faculty.ecnu.edu.cn/s/641/main.jspy Education 1999-2003
Title. Author(s)Takagi, Jun; Kamon, Akihiro; Ishiyama, Tatsuo; Miyau. CitationSynlett, 2002(11): Issue Date Doc URL.
Title Synthesis of β-boryl-α,β-unsaturated Carbonyl Compou Bis(pinacolato)diboron with Vinyl Triflates Author(s)Takagi, Jun; Kamon, Akihiro; Ishiyama, Tatsuo; Miyau CitationSynlett, 2002(11): 1880-1882
Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide
General Papers ARKIVC 2008 (xii) 103-108 Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide Ling He a,b, Qin Wang a, Guo-Chuan Zhou b, Lei Guo b, and Xiao-Qi
Fe-Catalyzed reactions of 2-chloro-1,7-dienes and allylmalonates
Fe-Catalyzed reactions of 2-chloro-1,7-dienes and allylmalonates David Nečas a, Pavel Drabina b, Miloš Sedlák b and Martin Kotora a,c a Department of Organic and Nuclear Chemistry, and Center for Structural
Organocopper Chemistry
rganocopper Chemistry ave a great historical importance, but still remain highly useful reactions. If not the first organometallic reactions developed they are among the first. Most often used in conjugate
1,2-dihalogenoethylene: a general substituted (E)-allylsilanes. CitationTetrahedron Letters, 45(24): 4677-
\n Title Cobalt-catalyzed mono-coupling of,-dihalogenoethylene: a general substituted (E)-allylsilanes KAMACHI, Taku; KUNO, Akiko; MATSUN Author(s) 専太郎 ; OKAMOTO, Sentaro CitationTetrahedron Letters, ():
Short Literature Presentation 10/4/2010 Erika A. Crane
Copper-Catalyzed Enantioselective Synthesis of trans-1- Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Additions-Intramolecular Enolate Trapping artog, T. D.; Rudolph, A.; Macia B.; Minnaard, A.
Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds*
Pure Appl. Chem., Vol. 72, No. 9, pp. 1715 1719, 2000. 2000 IUPAC Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds* O. G. Kulinkovich
Radical cascade reactions triggered by single electron transfer
Radical cascade reactions triggered by single electron transfer Reporter: Leming Wang Supervisor: Prof. Yong Huang 2017.11.13 Mateusz P. Plesniak, Huan-Ming Huang and David J. Procter; Nature Reviews Chemistry
sp 3 C-H Alkylation with Olefins Yan Xu Dec. 3, 2014
sp 3 C-H Alkylation with Olefins, Yan Xu Dec. 3, 2014 1) sp 3 C-H Alkylation via Directed C-H activation 2) Hydroaminoalkylation (still via C-H activation) 3) Hydrohydroxyalkylation (via radical chemistry)
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
Transition-metal-catalyzed reactions of carbon heteroatom bond formation by substitution and addition processes*
Pure Appl. Chem., Vol. 77, No. 12, pp. 2021 2027, 2005. DOI: 10.1351/pac200577122021 2005 IUPAC Transition-metal-catalyzed reactions of carbon heteroatom bond formation by substitution and addition processes*
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
Review. Frank Glorius & His Rh(III) C-H Activation. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21
Review Frank Glorius & His Rh(III) C-H Activation Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21 Author Introduction Prof. Dr. Frank Glorius 1972 Born 1991-1992 Military service
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
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*
Cambrian Explosion, Complex Eukaryotic Organism, Ozonosphere 3
Reporter: Wang Yuefan Reporter: Wang Yuefan Supervisor: Prof. Yang Zhen Supervisor: Prof. Yang Zhen Prof. Chen Jiahua Prof. Chen Jiahua 1 2011-12-2727 2011-02 2012-03 02-25 03-23 25 Content Preface Nature
University of Groningen
University of Groningen Catalytic Direct Cross-Coupling of Organolithium Compounds with Aryl Chlorides Hornillos, Valentin; Giannerini, Massimo; Vila, Carlos; Fananas-Mastral, Martin; Feringa, Ben L. Published
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
The Chemistry of Organozinc Reagent a long story. Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd.
The Chemistry of Organozinc Reagent a long story Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd. 2013 2 Content Introduction Reactions of Organozinc reagent
The mechanism of Ni(iPr pybox) complexes as asymmetric Negishi C C coupling catalysts
150 Chapter 5 The mechanism of Ni(iPr pybox) complexes as asymmetric Negishi C C coupling catalysts 5.1 Abstract The 2,6-bis(4-isopropyl-2-oxazolin-2-yl)pyridine (ipr-pybox) ligand, when combined with
Chem 634. Metal Mediated Substitution Chemistry. Reading: Heg Ch 1 2 (handout), CS-B 7.1, , 11.3, Grossman Ch 6
Chem 634 tal diated Substitution Chemistry eading: Heg Ch 1 2 (handout), CS-B 7.1, 8.2 8.3, 11.3, Grossman Ch 6 Announcements Problem Set 1 due NW. Mary Beth Kramer Lectureship 101 Brown Laboratory September
Regioselective Reductive Cross-Coupling Reaction
Lit. Seminar. 2010. 6.16 Shinsuke Mouri (D3) Regioselective Reductive Cross-Coupling Reaction Glenn C. Micalizio obtained a Ph.D. at the University of Michigan in 2001 under the supervision of Professor
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters The MIT Faculty has made this article openly available. Please share how this access benefits you.
Joseph Salamoun Current Literature 11/21/15 Wipf Group
Joseph Salamoun Current Literature 11/21/15 Wipf Group Joe Salamoun @ Wipf Group Page 1 of 16 12/29/2015 The mechanism of the oxidative addition-transmetallation-reductive elimination process is very complex
Halogen Bond Applications in Organic Synthesis. Literature Seminar 2018/7/14 M1 Katsuya Maruyama
Halogen Bond Applications in Organic Synthesis Literature Seminar 2018/7/14 M1 Katsuya Maruyama 1 Contents 1. Introduction 2. Property of Halogen Bond 3. Application to Organic Synthesis 2 1. Introduction
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
PHOTOCATALYSIS: FORMATIONS OF RINGS
PHOTOCATALYSIS: FORMATIONS OF RINGS Zachery Matesich 15 April 2014 Roadmap 2 Photoredox Catalysis Cyclizations Reductive Oxidative Redox-neutral Electron Transfer Conclusion http://www.meta-synthesis.com/webbook/11_five/five.html
Lecture 6: Transition-Metal Catalysed C-C Bond Formation
Lecture 6: Transition-Metal Catalysed C-C Bond Formation (a) Asymmetric allylic substitution 1 u - d u (b) Asymmetric eck reaction 2 3 Ar- d (0) Ar 2 3 (c) Asymmetric olefin metathesis alladium π-allyl
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction. Eric Gillis 4/19/07
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction Eric Gillis 4/19/07 Quaternary stereocenters in complex small molecules Retrosynthetic
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.
Three Type Of Carbene Complexes
Three Type f arbene omplexes arbene complexes have formal metal-to-carbon double bonds. Several types are known. The reactivity of the carbene and how it contributes to the overall electron counting is
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
Chem 634 February 10, 2004 References- Week 1 (corresponding authors in bold font) Prof. Fox
Chem 634 February 10, 2004 eferences- Week 1 (corresponding authors in bold font) Prof. Fox 1) Activation of Grignard eagents: Lai, Y. H. Synthesis 1981, 585. 2) S Li Li Screttas, C. G.; Micha-Screttas,
Enantioselective Protonations
Enantioselective Protonations Marc Timo Gieseler 25.02.2013 15.03.2013 Group Seminar AK Kalesse 1 verview Introduction Enantioselective Protonation of Cyclic Substrates Enantioselective Protonation of
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
Basic Organometallic Chemistry : Concepts, Syntheses, and Applications of Transition Metals. Table Of Contents: Foreword
Basic Organometallic Chemistry : Concepts, Syntheses, and Applications of Transition Metals Table Of Contents: Foreword v Preface vii List of abbreviations ix Chapter 1 Introduction 1 (15) 1.1 What is
Organic Reactions catalyzed by rhenium carbonyl complexes
Organic Reactions catalyzed by rhenium carbonyl complexes Fanyang Mo Dong group seminar Feb. 26, 2014 Ref: Kuninobu, Y.; Takai, K. Chem Rev. 2011, 111, 1938. 1 Accidentally found by Ogawa in 1908, and
Chromium Arene Complexes
Go through Reviews Chem. Reviews Chem. Soc. Reviews Book by Prof. A. J. Elias Chromium Arene Complexes Complexation of Cr(CO) 3 with ARENES Chromium arene complexes Metal complexation is appealing in organic
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry.
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry. 1] Development of Asymmetric Catalysis 2] Total Synthesis of Natural products 3] Development of Novel Protecting-Group-Free
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group. Lei Zhang 03/23/2016 Dong Group
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group Lei Zhang 03/23/2016 Dong Group Content 1 Alkyne involved Annulation in Hua group 2 3 4 Brief Introduction of Internal Oxidants
Sonogashira Couplings of Aryl Bromides: Room Temperature, Water Only, No Copper
Sonogashira Couplings of Aryl omides: Room Temperature, Water nly, o Copper uce. Lipshutz, David W. Chung, and ian Rich rg.lett. ASAP Article Presentation By ora Jameson Current Lit 08/30/2008 ora Jameson