Issue 2, 2023

Synthetic application of chalcogenonium salts: beyond sulfonium

Abstract

The application of chalcogenonium salts in organic synthesis has grown enormously in the past decades since the discovery of the methyltransferase enzyme cofactor S-adenosyl-L-methionine (SAM), featuring a sulfonium center as the reactive functional group. Chalcogenonium salts can be employed as alkylating agents, sources of ylides and carbon-centered radicals, partners for metal-catalyzed cross-coupling reactions and organocatalysts. Herein, we will focus the discussion on heavier chalcogenonium salts (selenonium and telluronium), presenting their utility in synthetic organic transformations and, whenever possible, drawing comparisons in terms of reactivity and selectivity with the respective sulfonium analogues.

Graphical abstract: Synthetic application of chalcogenonium salts: beyond sulfonium

Article information

Article type
Review Article
Submitted
05 10 2022
Accepted
03 12 2022
First published
06 12 2022

Org. Biomol. Chem., 2023,21, 223-236

Synthetic application of chalcogenonium salts: beyond sulfonium

A. Y. Bastidas Ángel, P. R. O. Campos and E. E. Alberto, Org. Biomol. Chem., 2023, 21, 223 DOI: 10.1039/D2OB01822E

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