Issue 7, 2022

Rhodium-catalyzed denitrogenative gem-difunctionalization of pyridotriazoles with thioesters: formal carbene insertion into C(O)–S bonds

Abstract

A formal carbene insertion into C(O)–S bonds to access α-quaternary pyridines was achieved via a rhodium(II)-catalyzed in situ formation of sulfonium ylides from pyridotriazoles with thioesters followed by acyl group migration. This protocol has enabled an efficient denitrogenative gem-acylthiolation of pyridotriazoles to incorporate an acyl, pyridyl, and sulfur-substituted quaternary carbon center with high selectivity, broad substrate scope, and good functional group tolerance.

Graphical abstract: Rhodium-catalyzed denitrogenative gem-difunctionalization of pyridotriazoles with thioesters: formal carbene insertion into C(O)–S bonds

Supplementary files

Article information

Article type
Communication
Submitted
27 Oct 2021
Accepted
17 Dec 2021
First published
18 Dec 2021

Chem. Commun., 2022,58, 1017-1020

Rhodium-catalyzed denitrogenative gem-difunctionalization of pyridotriazoles with thioesters: formal carbene insertion into C(O)–S bonds

Z. Gao, D. Jiang, B. Li and B. Wang, Chem. Commun., 2022, 58, 1017 DOI: 10.1039/D1CC06041D

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