Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction

被引：7

作者：

Hewitt, Kirsten A. ^{[1
]}

Herbert, Claire A. ^{[1
]}

Jarvo, Elizabeth R. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92617 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 32期

关键词：

UNACTIVATED ALKYL-HALIDES; REDUCTIVE DICARBOFUNCTIONALIZATION; CASCADE; SECONDARY; DIFUNCTIONALIZATION; ALKENYLATION; CHLORIDES; OLEFINS; ALKENES;

D O I：

10.1021/acs.orglett.2c02481

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that indicate this reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds through radical intermediates.

引用

页码：6093 / 6098

页数：6

共 97 条

[1] Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes [J].

Anthony, David ;

Lin, Qiao ;

Baudet, Judith ;

Diao, Tianning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3198-3202

[2] Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations [J].

Badir, Shorouk O. ;

Molandert, Gary A. .

CHEM, 2020, 6 (06) :1327-1339

[3] Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future [J].

Campeau, Louis-Charles ;

Hazari, Nilay .

ORGANOMETALLICS, 2019, 38 (01) :3-35

[4] A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study [J].

Chen, Pan-Pan ;

Lucas, Erika L. ;

Greene, Margaret A. ;

Zhang, Shuo-Qing ;

Tollefson, Emily J. ;

Erickson, Lucas W. ;

Taylor, Buck L. H. ;

Jarvo, Elizabeth R. ;

Hong, Xin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (14) :5835-5855

[5] Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration [J].

DeAngelis, Andrew ;

Panish, Robert ;

Fox, Joseph M. .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (01) :115-127

[6] Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes [J].

Derosa, Joseph ;

Apolinar, Omar ;

Kang, Taeho ;

Tran, Van T. ;

Engle, Keary M. .

CHEMICAL SCIENCE, 2020, 11 (17) :4287-4296

[7]

Derosa J, 2018, ALDRICHIM ACTA, V51, P21

[8] Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization [J].

Diccianni, Justin ;

Lin, Qiao ;

Diao, Tianning .

ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) :906-919

[9] Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction [J].

Diccianni, Justin B. ;

Katigbak, Joseph ;

Hu, Chunhua ;

Diao, Tianning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (04) :1788-1796

[10] Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes [J].

Do, Hien-Quang ;

Chandrashekar, E. R. R. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) :16288-16291

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