Synlett 2023; 34(09): 990-1000
DOI: 10.1055/a-1983-2038
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Cobalt-Catalyzed Alkynylation of Organic Compounds: Hydroalkynylation, Dehydrogenative Alkynylation, and Reductive Alkynylation

Yohei Ueda
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
,
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
,
Kazushi Mashima
b   Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan
› Author Affiliations
Part of our works described in this review was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant JP15H05808 (Precisely Designed Catalysis with Customized Scaffolding) and Grant JP22H02076 (Grant-in-Aid for Scientific Research B) to K.M.


Abstract

Cobalt-catalyzed hydroalkynylation of alkynes, alkenes, and imines affords internal alkynes with various functional groups adjacent to the carbon–carbon triple bond moiety in an atom-economical manner. In addition, cross-coupling of in situ generated alkynylcobalt species from terminal alkynes, haloalkynes, and metal acetylides with (hetero)aromatic compounds and organic halides selectively provides various internal aryl- and alkylalkynes.

1 Introduction

2 Hydroalkynylation of Alkynes for 1,3-Enyne Synthesis

3 Hydroalkynylation of Polar and Nonpolar Double Bonds

4 Dehydrogenative Cross-Coupling Reaction Using Terminal Alkynes with Aromatic Compounds

5 Cross-Coupling Reactions Using Haloalkynes as the Coupling Partners

6 Cross-Coupling Reactions Using Metal Acetylides

7 Conclusion



Publication History

Received: 20 October 2022

Accepted after revision: 21 November 2022

Accepted Manuscript online:
21 November 2022

Article published online:
11 January 2023

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