Issue 95, 2024

CO insertion enabled γ-C(sp3)–H heteroarylative carbonylation of tertiary alcohols via heteroaryl migration

Abstract

The direct functionalization of remote C(sp3)–H is valuable but challenging, and is even more difficult to achieve than the γ-C(sp3)–H functionalization of alcohols. Among the strategies, hydrogen atom transfer (HAT) is one of the solutions for such transformations. Herein, we designed a migration reaction involving carbon monoxide, forming an alkoxy radical by photocatalysis, and used carbon monoxide to extend the carbon chain to provide a site for the migration of heteroaryl groups, which makes 1,4-HAT more advantageous, and we relied on this strategy to successfully achieve the synthesis of 1,4-dicarbonyl compounds by γ-C(sp3) functionalization of alcohols.

Graphical abstract: CO insertion enabled γ-C(sp3)–H heteroarylative carbonylation of tertiary alcohols via heteroaryl migration

Supplementary files

Article information

Article type
Communication
Submitted
10 Oct 2024
Accepted
04 Nov 2024
First published
04 Nov 2024
This article is Open Access
Creative Commons BY license

Chem. Commun., 2024,60, 14034-14036

CO insertion enabled γ-C(sp3)–H heteroarylative carbonylation of tertiary alcohols via heteroaryl migration

X. Qi, Y. Wang and X. Wu, Chem. Commun., 2024, 60, 14034 DOI: 10.1039/D4CC05361C

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