Issue 5, 2023

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Abstract

Transition metal-catalyzed cross-coupling of sp2 C–H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction of C–C and C–heteroatom bonds in organic synthesis. Despite the popularity of diazo compounds as coupling partners in C–H activation, they pose serious safety and stability issues due to potential exothermic reactions linked with the release of N2 gas. However, compared with diazo compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used in industrial scales, and easier/safer to prepare. Therefore, recent years have witnessed an upsurge in employing α-carbonyl sulfoxonium ylides as an alternative carbene surrogate in transition metal-catalyzed C–H activation. Unlike diazo compounds, α-carbonyl sulfoxonium ylides contain inherent potential to serve as a coupling partner as well as a weak directing group. This review will summarize the progress made in both categories of reactions.

Graphical abstract: α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

  • This article is part of the themed collection: New Talent

Article information

Article type
Review Article
Submitted
07 Oct 2022
Accepted
05 Dec 2022
First published
06 Dec 2022

Org. Biomol. Chem., 2023,21, 879-909

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

A. Singh, S. Kumar and C. M. R. Volla, Org. Biomol. Chem., 2023, 21, 879 DOI: 10.1039/D2OB01835G

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