The Chemistry of Organozinc Reagent a long story. Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd.
|
|
|
- Kerry Higgins
- 5 years ago
- Views:
Transcription
1 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 2 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
3 3 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
4 Introduction Organozinc compound is the one contain carbon to zinc chemical bonds. Organozinc compounds are the first organometallic compounds ever made. In 1849, Edward Frankland prepared diethylzinc by heating ethyl iodide with zinc metal in a Carius tube. Frankland, E. Liebigs Ann. Chem., 1849, 71, 171 and
5 Introduction In 1887, S. Reformatsky utilized zinc metal, iodoacetic acid ethyl ester reacted with acetone. Reformatsky, S. N.; Ber. Dtsch. Chem. Ges., 1887, 20, Organozinc reagent was replaced by organomagnesium compound due to its very low reactivity toward most organic electrophiles. In 1942, Hunsdiecker first recognized this and prepared several organozinc iodides bearing an ester functional group. Hunsdiecker, H.; Erlbach, H.; Vogt, E. German patent ,
6 Introduction In 1958, H. E. Simmones and R. D. Smith first utilized CH 2 I 2 in the presence of Cu-Zn couple to convert unfunctionalized alkenes to cyclopropanes. Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5232 In 1980s, organozinc compounds are prone to undergo a large range of transmetalations with many transition metal salts leading to highly reactive intermediate. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93,
7 7 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
8 8 Organozinc reagents Simmons-Smith cyclopropanation No TM-catalyzed reactions TM-catalyzed reactions Rearrangement reactions
9 9 Organozinc reagents Simmons-Smith cyclopropanation No TM-catalyzed reactions TM-catalyzed reactions Rearrangement reactions
10 Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973, 46, 892. Denmark, S. E.; Edwards, J. P. J. Org. Chem., 1991, 56, Organozinc reagents Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, Furukawa, J.; et al. Tetrahedron Lett. 1966, 7, 3353.
11 Organozinc reagents Lorenz, J. C.; Long, J.; Yang, Z.; Xue, S.; Xie, Y.; Shi, Y. J. Org. Chem. 2004, 69,
12 Organozinc reagents The Chemistry of Organozinc Compounds (Eds. Z. Rappoport and I. Marek), John Wiley & Sons: Chichester, UK, 2006, P240 Fletcher, R. J.; Motherwell, W. B.; Popkin, M. E.; J. Chem. Soc., Chem. Commun., 1998,
13 Organozinc reagents The Chemistry of Organozinc Compounds (Eds. Z. Rappoport and I. Marek), John Wiley & Sons: Chichester, UK,
14 Organozinc reagents Charette, A. B.; Juteau, H. J. Am. Chem. Soc., 1994, 116, Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc., 1998, 120, Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S.; Tetrahedron Lett., 1992, 33, Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron, 1995, 51,
15 15 Organozinc reagents Simmons-Smith cyclopropanation No TM-catalyzed reactions TM-catalyzed reactions Rearrangement reactions
16 16 Organozinc reagents reactivity order of organo zinc reagents Suzuki, M.; Koyano, H.; Morita, Y. ; Noyori, R. Synlett, 1989, 22. Takahashi, T. ; Nakazawa, M.; Kanoh, M.; Yamamoto, K. Tetrahedron Lett., 1990, 31, 7349 Arisawa, M.; Torisawa, Y.; Kawahara, M.; Yamanaka, M.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1997, 62, 4327.
17 17 Organozinc reagents Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron, 1994,50, Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc., 1987, 109, 7111.
18 Organozinc reagents a) Kaneko, T.; et al. J. Am. Chem. Soc., 1988, 110, 7877.; b) Harms, K.; et al. Chem. Ber., 1992, 125, 1191 c) Kellogg, R. M.; et al. Tetrahedron: Asymmetry, 1995, 6, Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature, 1995, 378,
19 19 Organozinc reagents Simmons-Smith cyclopropanation No TM-catalyzed reactions TM-catalyzed reactions Rearrangement reactions
20 Organozinc reagents 20
21 Organozinc reagents Transmetalation to Cu Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, AchyuthaRao, S.; Chou, T. S.; Schipor, I.; Knochel, P. Tetrahedron, 1992, 48, Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem. Int. Ed. 1997, 36,
22 Organozinc reagents Transmetalation to Pd Deboves, H. J. C.; Montalbetti, A. G. N.; Jackson, R. F. W. J. Chem. Soc. Perkin Trans. 1, 2001, 1876 Watanabe, T.; Sakai, M.; Miyaura, N.; Suzuki, A. J. Chem. Soc. Chem. Commun. 1994, 467 Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39,
23 23 Organozinc reagents Simmons-Smith cyclopropanation No TM-catalyzed reactions TM-catalyzed reactions Rearrangement reactions
24 Organozinc reagents 1,2-metallate rearrangments Harada, T.; Katauhira, T.; Oku, A. J. Org. Chem., 1992, 57, Harada, T.; Katsuhira, T.; Hara, D.; Kotani, Y.; Maejima, K.; Kaji, R.; Oku, A. J. Org. Chem., 1993, 58, Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc., 1996, 118,
25 Organozinc reagents Allylmetalation J. F. Normant, Acc. Chem. Res., 2001, 34, 640. Zinca-ene-allene/Zinc-enolate cyclization Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem., 1995, 60, 863. Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem., 1998, 63,
26 26 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
27 27 Organozinc reagents Preparation of 1,1-bis-metallated reagent (a) Knochel, P.; Normant, J. F. Tetrahedron Lett., 1986, 27, 1039 and (b) Knochel, P.; Normant, J. F. Tetrahedron Lett., 1986, 27, 4427 and L. N. Nysted, US Patent, , 1975
28 Organozinc reagents Low basicity High reactivity Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett, 1998, 313. AÏssa, C.; Riveiros, R.; Ragot, J.; A. Fürstner J. Am. Chem. Soc.,2003, 125,
29 Organozinc reagents Yoshino, H.; Kobata, M.; Yamamoto, Y.; Oshima, K.; Matsubara, S. Chem. Lett., 2004, Knochel, P.; Normant, J. F. Tetrahedron Lett., 1986, 27,
30 30 Organozinc reagents Matsubara, S.; Toda, N.; Kobata, M.; K. Utimoto, Synlett, 2000, 987. Nomura, K.; Matsubara, S.; Angew. Chem., Int. Ed., 2005, 44, 5860.
31 Organozinc reagents Matsubara, S. J. Org. Synth. Soc. Jpn., 2000, 58, 118. Matsubara, S.; Otake, Y.; Hashimoto, Y.; Utimoto, K. Chem. Lett., 1999, 747. Matsubara, S.; Toda, N.; Kobata, M.; K. Utimoto, Synlett, 2000,
32 32 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
33 Summary 33
34 34 Content Introduction Reactions of Organozinc reagent Mono-Metalled reagent Bis-Metallated reagent Summary Acknowledgement
35 35 Acknowledgement Prof. Yang; Prof. Chen; Prof. Tang; Prof. Luo Dr. Li Yong; Mr. Jiang Yanlong; Mr. Zhou Shijie; Mr. Zhang Haoyu; Mr. Niu Zhe. Every lab mate in B628 All B647 lab mates All the members here
36 Thanks for your attention!!!
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
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,
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
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction Reporter: Zhang Sulei Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Prof. Tang Yefeng 2015-10-05 1 Contents Background
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
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
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:
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.
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
Selectivity and Natural Product Synthesis. Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang
Selectivity and Natural Product Synthesis Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity
Modern Synthetic Methods
Modern Synthetic Methods Dr. Dorian Didier dodich@cup.uni-muenchen.de Functionnalized Organometallic Reagents C-N, C-O and C-S Bond Formation Introduction to Organoboron Chemistry Introduction to Organosilicon
Recent Developments in the Chemistry of Polyvalent Iodine Compounds
Recent Developments in the Chemistry of Polyvalent Iodine Compounds Jiang Zhongping 2005-9-23 Content I. Introduction II. Iodine(III) Compounds III. Iodine(V) Compounds IV. Conclusions Introduction Why
Copper-mediated asymmetric transformations*
Pure Appl. Chem., Vol. 74, No. 1, pp. 37 42, 2002. 2002 IUPAC Copper-mediated asymmetric transformations* Alexandre Alexakis Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet,
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 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
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,
Dual enantioselective control by heterocycles of (S)-indoline derivatives*
Pure Appl. Chem., Vol. 77, No. 12, pp. 2053 2059, 2005. DOI: 10.1351/pac200577122053 2005 IUPAC Dual enantioselective control by heterocycles of (S)-indoline derivatives* Yong Hae Kim, Doo Young Jung,
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
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
First Row TM Catalyzed C-H Activation. Zhi Ren 2014/9/10
First Row TM Catalyzed C-H Activation Zhi Ren 2014/9/10 Outline 1. Introduction 2. Sc catalyzed C-H activation 3. Ti catalyzed C-H activation 4. V catalyzed C-H oxidation/fluorination 5. Mn catalyzed C-H
N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations
Angew. Chem. Int. Ed. 2017, 10.1002. 1 N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations Reporter: En Li Supervisor: Prof. Yong
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
The Story of Azadirachtin. Weiwu Ren
The Story of Azadirachtin Weiwu Ren 2015-12-17 Content 1 Introduction 2 Isolation and Structure Determination 3 Synthetic Study towards Azadirachtin 4 Total Synthesis of Azadirachtin Ley s Work Watanabe
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,
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
Alkyne Dicobalt Complexes in Organic Chemistry
Alkyne Dicobalt Complexes in Organic Chemistry Sun Baochuan Supervisors: Prof. Yang Prof. Chen Prof. Tang Cobalt - Co From German word kobald - evil spirits Atomic Number: 27 Group: 9 Period: 4 3d 7 4s
Mn Reagent & Organomanganese: Neglected Powerful Tool. Reporter: Li Zhuo Advisor: Prof. Yang Prof. Chen Prof. Tang
Mn Reagent & Organomanganese: Neglected Powerful Tool Reporter: Li Zhuo Advisor: Prof. Yang Prof. Chen Prof. Tang 1 Content Introduction Oxidation by Mn(VII) & Mn(IV) Epoxidation & Cyclopropanation Radical
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
CuI CuI eage lic R tal ome rgan gbr ommon
Common rganometallic eagents Li Et 2 Li Mg Et 2 Li alkyllithium rignard Mg Mg Li Zn TF ZnCl 2 TF dialkylzinc Zn 2 2 Zn Li CuI TF ganocuprate CuI 2 2 CuI common electrophile pairings ' Cl ' '' ' ' ' ' '
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.
Highly selective synthetic organic reactions utilizing cleavage of C-Cl bond
Highly selective synthetic organic reactions utilizing cleavage of C- bond SmI 2 Reformatsky rg. Lett. 2008, 10, 5453.) C- C-C C- C-C C- C-- C- Chem. Lett. 2009, 38, 1078. Sc(Tf) 3 (Chem. Lett. 2010, 39,
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
Supporting information. Double Reformatsky Reaction: Divergent Synthesis of δ-hydroxy-β-ketoesters
Supporting information Double Reformatsky Reaction: Divergent Synthesis of δ-hydroxy-β-ketoesters Masahiro Mineno,* Yasuhiro Sawai, Kazuaki Kanno, Naotaka Sawada and Hideya Mizufune Chemical Development
Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates
Pure & Appl. Chern., Vol. 70, No. 5, pp. 11 17-1 122, 1998. Printed in Great Britain. (0 1998 IUPAC Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates Mogens
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)
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
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
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
Protecing-Group-Free Synthesis. Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date:
Protecing-Group-Free Synthesis Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date: 2015.05.19 1 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples
Title. Author(s)Sawaguchi, Masanori; Ayuba, Shinichi; Hara, Shoji. CitationSynthesis, 2002(13): Issue Date Doc URL.
Title A Practical Synthetic Method for Iodoarene Difluorid Author(s)Sawaguchi, Masanori; Ayuba, Shinichi; Hara, Shoji CitationSynthesis, 2002(13): 1802-1803 Issue Date 2002-09 Doc URL http://www.thieme-chemistry.com/thieme-chemistry/jou
14.11 Alkane Synthesis Using Organocopper Reagents
14.11 Alkane Synthesis Using Organocopper Reagents Lithium Dialkylcuprates Lithium dialkylcuprates are useful synthetic reagents. They are prepared from alkyllithiums and a copper(i) halide. 2RLi + CuX
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)
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
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.
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
Career Review of Dean Toste I. 2015/9/9 Zhi Ren
Career Review of Dean Toste I 2015/9/9 Zhi Ren Introduction F. Dean Toste, now in UC Berkeley Career: Full Professor since 2009-now Associate Professor 2006-2009 Assistant Professor 2002-2006 Faculty Scientist
Morita Baylis Hillman Reaction. Aaron C. Smith 11/10/04
Morita Baylis Hillman Reaction Aaron C. Smith 11/10/04 Outline 1. Background 2. Development of Asymmetric Variants 3. Aza-Baylis Hillman Reaction 4. Applications of Baylis Hillman Adducts Outline 1. Background
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
Working with Hazardous Chemicals
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
Topic Review Group meeting
Topic Review Group meeting Memory of chirality Christian Gloor Based on: Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1. Table of content > Definitions of memory of chirality > Types of chirality
I. Introduction. II. Retrosynthetic Analysis. Andrew Baggett. Liu lab
Total Synthesis of Limonin Shuji Yamashita,* Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, Masahiro Hirama Tohoku University, Department of Chemistry, Aramaki-aza aoba, Aoba-ku, Sendai 980-8578
Mechanism and Transition-State Structures for Nickel- Catalyzed Reductive AlkyneAldehyde Coupling Reactions
Mechanism and Transition-State Structures for Nickel- Catalyzed Reductive AlkyneAldehyde Coupling Reactions The MIT Faculty has made this article openly available. Please share how this access benefits
Hypervalent Iodine(III): Property and Reactivity. Penghao Chen g Dong Group Seminar October, 21 st, 2015
Hypervalent Iodine(III): Property and Reactivity Penghao Chen g Dong Group Seminar October, 21 st, 2015 Structure and Nomenclature Aryl λ 3 iodanes: L I L L : hypervalent bond with a pure 5p orbital Ar
Mechanistic Implications in the Morita Baylis Hillman Alkylation: Isolation and Characterization of an Intermediate
Mechanistic Implications in the Morita Baylis Hillman Alkylation: Isolation and Characterization of an Intermediate M. E. Krafft,* T. F. N. Haxell, K. A. Seibert, and K. A. Abboud Department of Chemistry
Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines
Literature Report V Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines Reporter Checker Date : Xiao-Yong Zhai : Xin-Wei Wang : 2018-04-02 You,
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
The Vinylogous Aldol Reaction
The Vinylogous Aldol Reaction Reporter: Sixuan Meng Supervisor: Prof. Huang 2013-09-09 Zanardi, F. et al. Chem. Rev. 2000, 100, 1929 Zanardi, F. et al.. Chem. Rev. 2011, 111, 3076 Introduction 2 3 Regiochemical
Synthetically useful extrusion reactions in organic chemistry
Synthetically useful extrusion reactions in organic chemistry Reporter: Sun Baochuan Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Extrusion Reactions Extrusion Reaction: An atom or group Y connected
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
Citation for published version (APA): Bos, P. H. (2012). Novel asymmetric copper-catalysed transformations Groningen: s.n.
University of Groningen Novel asymmetric copper-catalysed transformations Bos, Pieter Harm IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from
Dr. P. Wipf Chem /26/2007
I. Basic Principles I-L. Radicals & Carbenes Features of Radical Reactions Review: Curran, D. P. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon Press: Oxford, 1991; Vol.
Coordination-enabled one-step assembly of. ultrathin, hybrid microcapsules with. weak ph-response
Supporting Information Coordination-enabled one-step assembly of ultrathin, hybrid microcapsules with weak ph-response Chen Yang,, Hong Wu,, Xiao Yang,, Jiafu Shi*,,, Xiaoli Wang,, Shaohua Zhang, and Zhongyi
Lewis Base Catalysis in Organic Synthesis
Hu Group Lewis Base Catalysis in Organic Synthesis Group Meeting Yuwen Zeng Sep. 28 th, 2014 Introduction Definitions Basic concepts Presentation Outline Lewis base catalysis: n- * Interactions Electrophilic
C H activation of aliphatic amines without unnecessary mask M2 Takaya Togo
C H activation of aliphatic amines without unnecessary mask 2017.11.25 M2 Takaya Togo 1 Outline 1.Introduction 2.Free amines as DG Discovery of new activation mode Mechanistic studies Application of the
Nucleophilic Heterocyclic Carbene Catalysis. Nathan Werner Denmark Group Meeting September 22 th, 2009
Nucleophilic Heterocyclic Carbene Catalysis Nathan Werner Denmark Group Meeting September 22 th, 2009 Thiamine Thiamine Vitamin B 1 The first water-soluble vitamin described Is naturally synthesized by
Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang!
1! Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang! 2! utline! 1. Brief Introduction! 2. ucleophilic Dominoes! 3. Electrophilc Dominoes! 4. Radical
sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito
1 sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito 2016. 1. 30 1. Introduction 2 About Carbene 3 Brief history of carbene (~2000) Carbene Neutral compounds featuring a divalent carbon atom with only
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
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY Pierre Deslongchamps (version du 16 février 2010) Cf. pour le livre: http://pages.usherbrooke.ca/pdeslongchamps/cv.htm 1 SECTION 8 Stereoelectronic
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
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
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,
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
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*
Iron Catalysis in Organic Synthesis Multitasking Champion. Current literature Andrey Kuzovlev
Iron Catalysis in Organic Synthesis Multitasking Champion Current literature Andrey Kuzovlev 02.03.2017 Introduction Readily available, cheap, relatively nontoxic, 1.300 ppm residual iron is acceptable
HONORS ORGANIC CHEM. HAHS MRS. RICHARDS
NRS RGANIC CEM. AS MRS. RICARDS RGANIC CEMISTRY: FINAL EXAM REVIEW List of Topics: While the exam will specifically focus on material from Quarter 2, an understanding of several important concepts from
molecules ISSN
Molecules 001, 6, 44-447 molecules ISSN 140-3049 http://www.mdpi.org Facile and Fast Pinacol Rearrangement by All 3 in the Solid State Parviz Rashidi-Ranjbar* and Ebrahim Kianmehr Department of hemistry
Dyotropic Rearrangements. Presented by Matthew Burk
Dyotropic Rearrangements Presented by Matthew Burk 5-11-2010 What is a Dyotropic Rearrangement? A process in which two σ-bonds simultaneously migrate intramolecularly Type 1 2 σ bonds exchange their positions
Recent (and Not-So-Recent) Applications of Geminal Dianions. Danielle Jacobs Crimmins Group Meeting 3/7/07
Recent (and Not-So-Recent) Applications of Geminal Dianions Danielle Jacobs Crimmins Group Meeting 3/7/07 Carbon-Based Dianions Important intermediates for carbon-carbon bond forming reactions Nomenclature
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.
Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~
Literature Seminar 2010.5.26 Yao u(2) Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~ Contents: 1. Yong-Qiang Tu's Profile 2.LatestWorkofProfessorTu 2-1. 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)
Lycopodine & Huperzine A Story of Lycopodium Alkaloids
Lycopodine & Huperzine A Story of Lycopodium Alkaloids Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2014/12/3 Content Background Synthetic Studies of Lycopodine An AChEI Huperzine A Summury
April 2002 CUME Organic Chemistry Department of Chemistry University of Missouri Columbia Saturday, April 6th, 2002 Dr.
April 2002 CUME Organic Chemistry Department of Chemistry University of Missouri Columbia Saturday, April 6th, 2002 Dr. Rainer Glaser Announced Reading: Prins Cyclization Reactions 1 Question 1. Aldol-Prins
Palladium-catalyzed cross-addition of triisopropylsilylacetylene to unactivated alkynes*
Pure Appl. Chem., Vol. 80, No. 5, pp. 1161 1166, 2008. doi:10.1351/pac200880051161 2008 IUPAC Palladium-catalyzed cross-addition of triisopropylsilylacetylene to unactivated alkynes* Naofumi Tsukada, Satoshi
COPPER-CATALYZED, ENANTIOSELECTIVE CONJUGATE ADDITION. Reported by Monica Jo Patten December 6, 2004
CPPE-CATALYZED, EATISELECTIVE CJUGATE ADDITI eported by Monica Jo Patten December 6, 2004 ITDUCTI Conjugate addition of carbon nucleophiles to α,β-unsaturated electrophiles is an essential carbon-carbon
Ynolate Chemistry. Jeff Kallemeyn October 22, 2002
Ynolate Chemistry While enolates have numbered among the most important reagents of organic chemistry for more than a century, ynolates have hitherto remained unknown although their chemistry should be
Supporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information for Chiral Brönsted Acid Catalyzed Asymmetric Baeyer-Villiger Reaction of 3-Substituted Cyclobutanones Using Aqueous
The application of ligands with planar chirality in asymmetric synthesis*
Pure Appl. Chem., Vol. 71, No. 8, pp. 1401±1405, 1999. Printed in Great Britain. q 1999 IUPAC The application of ligands with planar chirality in asymmetric synthesis* Li-Xin Dai,² Xue-Long Hou, Wei-Ping
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion- 3/4 4/5 5/6 6/7 endo- -dig exo- endo- -trig exo- endo- -tet exo-
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion - 3/4 4/5 5/6 6/7 -trig Supervisors: Prof. Yang Prof. Chen -tet Prof. Tang Introduction (Sir) Jack Baldwin 1938, Born,
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
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.
Synthesis of Cyclopropanes
Synthesis of Cyclopropanes Topic Review Key references: M. Ohkita, S. Nishida and T. Tsuji, in PATAI'S Chemistry of Functional Groups, John Wiley & Sons, Ltd, 2009. J.-i. Yoshida, Synlett, 2006, 515-526.
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.
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,
Working with Hazardous Chemicals
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training
Chiral Ionic Liquids (CILs) in Asymmetric Synthesis: The story so far.
Chiral Ionic Liquids (CILs) in Asymmetric Synthesis: The story so far. Literature Presentation Aman Desai 06.16.06 1. Angew. Chem. Int. Ed. 2006, 45, 3689 2. Angew. Chem. Int. Ed. 2006, 45, 3093 3. Tetrahedron:
VI. Metal alkyls from oxidative addition / insertion
V. Metal alkyls from oxidative addition / insertion A. Carbonylation - C insertion very facile, metal acyls easily cleaved, all substrates which undergo oxidative addition can in principle be carbonylated.
i-pr 2 Zn CHO N Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. Engl. 2004, 43, 4490
Asymmetric Synthesis Utilizing Circularly Polarized Light Mediated by the otoequilibration of Chiral lefins in Conjuction with Asymmetric Autocatalysis l-cpl r-cpl (S) () Sato, I.; Sugie,.; Matsueda, Y.;