Literature DB >> 29095598

Cu-Catalyzed Three-Component Carboamination of Alkenes.

Samuel N Gockel1, Travis L Buchanan1, Kami L Hull1.   

Abstract

Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening to forge the C-N bond.

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Year:  2017        PMID: 29095598      PMCID: PMC6092015          DOI: 10.1021/jacs.7b10529

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  45 in total

1.  Atom transfer radical polymerization.

Authors:  K Matyjaszewski; J Xia
Journal:  Chem Rev       Date:  2001-09       Impact factor: 60.622

2.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

3.  Free-radical carbon-carbon bond formation in organic synthesis.

Authors:  D J Hart
Journal:  Science       Date:  1984-03-02       Impact factor: 47.728

4.  Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Authors:  Chanchamnan Um; Sherry R Chemler
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

5.  Organic Photoredox Catalysis.

Authors:  Nathan A Romero; David A Nicewicz
Journal:  Chem Rev       Date:  2016-06-10       Impact factor: 60.622

6.  Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Authors:  Zachary J Garlets; Derick R White; John P Wolfe
Journal:  Asian J Org Chem       Date:  2017-03-10       Impact factor: 3.319

Review 7.  Olefinic C-H functionalization through radical alkenylation.

Authors:  Shan Tang; Kun Liu; Chao Liu; Aiwen Lei
Journal:  Chem Soc Rev       Date:  2015-03-07       Impact factor: 54.564

8.  Catalytic Alkene Carboaminations Enabled by Oxidative Proton-Coupled Electron Transfer.

Authors:  Gilbert J Choi; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2015-07-15       Impact factor: 15.419

9.  γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes.

Authors:  Nengbo Zhu; Ting Wang; Liang Ge; Yajun Li; Xinhao Zhang; Hongli Bao
Journal:  Org Lett       Date:  2017-09-01       Impact factor: 6.005

10.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419

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  14 in total

1.  Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors:  Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2018-01-05       Impact factor: 6.005

2.  Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Authors:  Jonathan J Kennedy-Ellis; Erik D Boldt; Sherry R Chemler
Journal:  Org Lett       Date:  2020-10-19       Impact factor: 6.005

3.  Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Authors:  Yungeun Kwon; Qiu Wang
Journal:  Org Lett       Date:  2020-05-08       Impact factor: 6.005

4.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

5.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers.

Authors:  Jian He; Caiyou Chen; Gregory C Fu; Jonas C Peters
Journal:  ACS Catal       Date:  2018-10-31       Impact factor: 13.084

6.  Copper-Catalyzed Synthesis of Hindered Ethers from α-Bromo Carbonyl Compounds.

Authors:  Zhe Zhou; Nicole Erin Behnke; László Kürti
Journal:  Org Lett       Date:  2018-08-16       Impact factor: 6.005

7.  Ti-Catalyzed and -Mediated Oxidative Amination Reactions.

Authors:  Ian A Tonks
Journal:  Acc Chem Res       Date:  2021-08-22       Impact factor: 24.466

8.  Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors:  Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal:  Organic Synth       Date:  2021

9.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

10.  Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay.

Authors:  Aijie Cai; Wenhao Yan; Xiaojun Zeng; Samson B Zacate; Tzu-Hsuan Chao; Jeanette A Krause; Mu-Jeng Cheng; Wei Liu
Journal:  Nat Commun       Date:  2021-06-01       Impact factor: 14.919

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