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Synthesis 2019; 51(03): 612-628
DOI: 10.1055/s-0037-1610328
DOI: 10.1055/s-0037-1610328
short review
Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis
We thank the Research Council of Norway (FRINATEK Grant No. 231706 and Centre of Excellence Grant No. 262695), the Tromsø Research Foundation (Grant No. TFS2016 KHH), and Nordforsk (Grant No. 85378). J.V. thanks the CHOCO-UiT (https://site.uit.no/choco/) research team PI: Kathrin H. Hopmann/A.Bayer for research and financial support.Further Information
Publication History
Received: 14 September 2018
Accepted after revision: 17 October 2018
Publication Date:
12 December 2018 (online)
Abstract
As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.
1 Introduction
2 Preparation of Sulfoxonium Ylides
3 Investigation for Carbenoid Formation from Sulfoxonium Ylide
4 X–H (X = N, O, S, C) Functionalization Reactions
5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides
6 Conclusion and Perspective
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