Issue 28, 2022

Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils

Abstract

A ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles has been developed to achieve the direct C–H formylmethylation of a diverse array of arylisoxazoles utilizing the isoxazole ring as the directing group. A simple manipulation of the established reaction conditions leads to the formation of fused-anthranils. Importantly, the vinylene carbonate functions as both a formylmethyl cation equivalent through a decarboxylation process and an acetylene equivalent. Control experiments were conducted to elucidate a plausible mechanism. This methodology is expected to provide a facile and expeditious approach for the synthesis of formylmethyl isoxazoles and fused-anthranils.

Graphical abstract: Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils

Supplementary files

Article information

Article type
Communication
Submitted
21 Feb 2022
Accepted
08 Mar 2022
First published
09 Mar 2022

Chem. Commun., 2022,58, 4476-4479

Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils

P. Kumar and M. Kapur, Chem. Commun., 2022, 58, 4476 DOI: 10.1039/D2CC01048H

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