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Synthesis 2022; 54(06): 1478-1502
DOI: 10.1055/a-1677-5971
DOI: 10.1055/a-1677-5971
short review
Alkylation Reactions with Alkylsulfonium Salts
Ze-Yu Tian
a
School of Materials Science and Engineering, Wuhan University of Technology, Wuhan, 430070, P. R. of China
b
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, P. R. of China
,
Yu Ma
b
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, P. R. of China
,
a
School of Materials Science and Engineering, Wuhan University of Technology, Wuhan, 430070, P. R. of China
b
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, P. R. of China
› Author AffiliationsWe thank Wuhan University of Technology, the ‘Hundred Talent’ Program of Hubei Province (China), and the Fundamental Research Funds for the Central Universities (2019-YB-002 and 2020-YB-003) for financial support.
Abstract
The application of alkylsulfonium salts as alkyl-transfer reagents in organic synthesis has reemerged over the past few years. Numerous heteroatom- and carbon-centered nucleophiles, alkenes, arenes, alkynes, organometallic reagents, and others are readily alkylated by alkylsulfonium salts under mild conditions. The reactions feature convenience, high efficiency, readily accessible and structurally diversified alkylation reagents, good functional group tolerance, and a wide range of substrate types, allowing the facile synthesis of various useful organic molecules from commercially available building blocks. This review summarizes alkylation reactions using either isolated or in situ formed alkylsulfonium salts via nucleophilic substitution, transition-metal-catalyzed reactions, and photoredox processes.
1 Introduction
2 General Methods for the Synthesis of Alkylsulfonium Salts
3 Electrophilic Alkylation Using Alkylsulfonium Salts
4 Transition-Metal-Catalyzed Alkylation Using Alkylsulfonium Salts
5 Photoredox-Catalyzed Alkylation Using Alkylsulfonium Salts
6 Conclusion
Publication History
Received: 30 September 2021
Accepted after revision: 25 October 2021
Accepted Manuscript online:
25 October 2021
Article published online:
12 January 2022
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Selected examples:
Selected paper and reviews:
Selected examples:
Selected examples:
Selected pioneer works:
Selected literature:
Selected examples:
Examples of use of aryl alkyl sulfonium salts as arylation reagents rather than alkylation ones: