Synthesis
DOI: 10.1055/a-1486-2158
short review

Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification

Biwen Gao
a  Department of Chemistry, Lishui University, No. 1, Xueyuan Road, Lishui City 323000, Zhejiang Province, P. R. of China
,
Danfeng Deng
a  Department of Chemistry, Lishui University, No. 1, Xueyuan Road, Lishui City 323000, Zhejiang Province, P. R. of China
,
a  Department of Chemistry, Lishui University, No. 1, Xueyuan Road, Lishui City 323000, Zhejiang Province, P. R. of China
,
Xiangyu Sun
b  Torch High Technology Industry Development Center, Ministry of Science & Technology, NO.18,Sanlihe District,Beijing,100045, P. R. of China
› Author Affiliations
We thank the Natural Science Foundation of Zhejiang Province (LQ18B020001) and the Foundation of University Student Innovation Program for financial support.


Abstract

Recent advances on the tandem difunctionalization of alkynes in the last decade (2010–2020) are summarized into five categories based on the type of mechanism: (1) radical addition and coupling for the synthesis of polysubstituted ketones and alkenes, (2) electrophilic addition of alkynes, (3) reactions mediated by haloalkynes or copper acetylides, (4) the preparation of cyclic compounds via radical processes, palladium-catalyzed reactions or conjugate additions, and (5) cyclic compounds as intermediates in ring openings. Herein, radical, electrophilic and nucleophilic reactions are discussed in detail. We hope this review will help to promote future research in this area.

1 Introduction

2 Radical Addition and Coupling

3 Electrophilic Addition

4 Reactions Mediated by Haloalkynes or Copper Acetylides

5 Cyclization

6 Cyclization and Ring Opening

7 Conclusions



Publication History

Received: 23 March 2021

Accepted after revision: 19 April 2021

Publication Date:
19 April 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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