Issue 83, 2023

Insights into the multifaceted applications of vinyl sulfoxonium ylides

Abstract

Sulfoxonium ylides are important synthetic precursors in various organic transformations. Their synthetic potential was well explored in the synthesis of various bioactive natural products and pharmaceuticals. Vinyl sulfoxonium ylide is a stabilized sulfoxonium ylide containing an electron-deficient alkene at the ylidic carbon. Similar to α-keto sulfoxonium ylides, these reagents can generate vinyl carbenes in the presence of metals under suitable conditions. These vinyl carbenes can be used for various organic transformations such as X–H (X = C, N, O, S) insertions, annulations, and rearrangement reactions. Due to the dipole structure of the vinyl sulfoxonium ylide, it can undergo electrophilic addition with electrophiles at the α-position. These reagents are used as synthons for various aromatic and heteroaromatic compound syntheses. Moreover, their stability and convenient handling make them potential replacements for thermally less stable vinyl diazo compounds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of vinyl sulfoxonium ylide-mediated transformations in the presence and absence of metal catalysis, and also give personal perspectives on the challenges and future scope for improving the application of vinyl sulfoxonium ylides.

Graphical abstract: Insights into the multifaceted applications of vinyl sulfoxonium ylides

Article information

Article type
Feature Article
Submitted
24 Aug 2023
Accepted
19 Sep 2023
First published
20 Sep 2023

Chem. Commun., 2023,59, 12411-12422

Insights into the multifaceted applications of vinyl sulfoxonium ylides

R. Sen, S. Bhardwaj, K. Bar, S. Deshwal and J. Vaitla, Chem. Commun., 2023, 59, 12411 DOI: 10.1039/D3CC04137A

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