Synlett 2018; 29(11): 1421-1429
DOI: 10.1055/s-0037-1609682
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© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Hydroboration and Borylation of Alkenes and Alkynes

Ziqing Zuo
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: huangzh@sioc.ac.cn
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Huanan Wen
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: huangzh@sioc.ac.cn
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Guixia Liu
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: huangzh@sioc.ac.cn
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Zheng Huang*
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: huangzh@sioc.ac.cn
› Author Affiliations

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (21432011, 21572255, 21732006)
Further Information

Publication History

Received: 21 March 2018

Accepted after revision: 21 March 2018

Publication Date:
23 April 2018 (online)


Abstract

Incorporation of the boryl moiety across a carbon–carbon multiple bond is a powerful method for the synthesis of organoboron compounds. This kind of transformation could be realized with high chemo-, regio-, and stereoselectivity by using an appropriate transition-metal catalyst. This account summarizes the latest advances from our group in the area of cobalt-catalyzed hydroboration and borylation of alkenes and alkynes, which lead to the formation of a variety of organoboron compounds, including alkylboronates, 1,1,1-tris(boronates), 1,1-diborylalkenes, and 1,1-diboronates.

1 Introduction

2 Cobalt-Catalyzed Hydroboration of Alkenes

3 Cobalt-Catalyzed Dehydrogenative Borylations-Hydroboration

4 Cobalt-Catalyzed Double Dehydrogenative Borylations of 1-Alkenes

5 Cobalt-Catalyzed Hydroboration of Terminal Alkynes

6 Summary and Outlook