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 ต.ค. 2565
Accepted
05 ธ.ค. 2565
First published
06 ธ.ค. 2565

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements