Issue 52, 2023

α-Diazo-λ3-iodanes and α-diazo sulfonium salts: the umpolung of diazo compounds

Abstract

This minireview aims to cover the developments of the last few years in the design of reagents able to accomplish the umpolung of the azomethine carbon in diazo compounds namely, α-diazo-λ3-iodanes and α-diazo sulfonium salts. Specifically, the routes available for their preparation and a classification of their unique reactivity patterns (either acting as equivalents of carbene-radical or carbene-carbocation synthons) are discussed. We also present a detailed overview of the synthetic utility of such species and, when possible, a critical comparation their reactivity and properties.

Graphical abstract: α-Diazo-λ3-iodanes and α-diazo sulfonium salts: the umpolung of diazo compounds

Article information

Article type
Feature Article
Submitted
02 apr 2023
Accepted
30 mei 2023
First published
06 jun 2023
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2023,59, 8032-8042

α-Diazo-λ3-iodanes and α-diazo sulfonium salts: the umpolung of diazo compounds

S. Timmann and M. Alcarazo, Chem. Commun., 2023, 59, 8032 DOI: 10.1039/D3CC01620J

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