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Synthesis 2015; 47(16): 2317-2346
DOI: 10.1055/s-0034-1378852
review
© Georg Thieme Verlag Stuttgart · New York

Coinage-Metal-Catalyzed Reactions of Propargylic Alcohols

Lin Zhang
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
,
Guichun Fang
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
,
Rapolu Kiran Kumar
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
,
Xihe Bi*
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
b   State Key Laboratory of Elemento-Organic Chemistry, Nankai University, 300071 Tianjin, P. R of China
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Further Information

Publication History

Received: 11 December 2014

Accepted after revision: 24 April 2015

Publication Date:
04 August 2015 (online)

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Abstract

Propargylic alcohols, which possess inherent alkynyl and hydroxyl functional groups, are one of the most valuable bifunctional building blocks in the field of organic synthesis. The simple generation and conversion of these compounds into various valuable products make propargylic alcohols a powerful tool for synthetic organic chemists. These conversions have been largely achieved using transition-metal-catalytic systems, especially those using coinage metals (i.e., copper, silver and gold). However, few reviews focusing on these transformations have been published. This review summarizes the chemistry of propargylic alcohol moiety based reactions controlled by coinage-metal-catalytic systems.

1 Introduction

2 Nucleophilic Substitution Reactions

3 Rearrangement Reactions

4 Cyclization Reactions

5 Miscellaneous Reactions

6 Conclusion

Key words

propargylic alcohols - coinage metals - nucleophilic substitution - rearrangement - cyclization