Transition-metal-free decarbonylation-oxidation of 3-arylbenzofuran-2(3 H)-ones: access to 2-hydroxybenzophenones

Beilstein J Org Chem. 2024 Oct 21:20:2655-2667. doi: 10.3762/bjoc.20.223. eCollection 2024.

Abstract

A transition-metal-free decarbonylation-oxidation protocol for the conversion of 3-arylbenzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions has been developed. NMR studies confirmed the role of in-situ-generated hydroperoxide in the conversion. The protocol was applied to a diverse range of substrates to access the target products in good to excellent yields. A structure-activity study for the 5-substituted-2-hydroxybenzophenones towards UV-protection abilities has been verified by mathematical calculations.

Keywords: 2-hydroxybenzophenone; UV-protection; decarbonylation–oxidation; hydroperoxide; transition-metal-free.