Synthesis 2013; 45(15): 2051-2069
DOI: 10.1055/s-0033-1339176
review
© Georg Thieme Verlag Stuttgart · New York

Carbon–Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles

Wei Liu
Department of Chemistry, State Key Laboratory of Pollution Control and Resource Reuse, Tongji University, 1239 Siping Lu, Shanghai 200092, P. R. of China   Fax: +86(21)65981376   Email: xmzhao08@mail.tongji.edu.cn
,
Xiaoming Zhao*
Department of Chemistry, State Key Laboratory of Pollution Control and Resource Reuse, Tongji University, 1239 Siping Lu, Shanghai 200092, P. R. of China   Fax: +86(21)65981376   Email: xmzhao08@mail.tongji.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 March 2013

Accepted after revision: 08 April 2013

Publication Date:
10 July 2013 (online)


Abstract

The development of practical approaches for the construction of carbon–sulfur bonds is of interest to scientists. In particular, carbon–sulfur bond formation by transition-metal-catalyzed allylations has been attracting great attention. Allylic sulfides are important substances owing to their broad applications in synthetic and pharmaceutical areas. The alkene and sulfur moieties in allylic sulfides can lead to numerous transformations. This review details the development of carbon–sulfur bond formation through palladium-catalyzed rearrangements, palladium-catalyzed allylations, ­iridium-catalyzed regio- and enantioselective allylations and miscellaneous metal-catalyzed allylic substitutions. Carbon–selenium bond formations via metal-catalyzed allylic substitutions are also reviewed.

1 Introduction

2 Carbon–Sulfur Bond Formation via Palladium-Catalyzed Reactions

2.1 Rearrangements of Allylic Substrates

2.2 Allylations

2.3 Asymmetric Allylations

3 Carbon–Sulfur Bond Formation via Iridium-Catalyzed Regio­- and Enantioselective Allylations

4 Carbon–Sulfur Bond Formation via Miscellaneous Metal-Catalyzed Reactions

4.1 Nickel

4.2 Ruthenium

4.3 Gallium

4.4 Iron

5 Carbon–Selenium Bond Formation via Metal-Catalyzed Allylic­ Substitutions

6 Conclusions

 
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