Photocatalytic dehydrogenative oxidation/amination of 2-alkyl benzamides under transition-metal-free conditions?

Organic Chemistry Frontiers Pub Date: 2023-07-24 DOI: 10.1039/D3QO00878A

Abstract

A mild pathway is reported herein for converting 2-alkyl benzamides into functionalized hydroxyisoindolines under visible light stimulation using oxygen as the sole terminal oxidant with synergistic interactions of eosin Y and nBu4NBr. Using this method over 56 examples of hydroxyisoindolines with various functional groups have been prepared in up to 92% yield. The practical value of this catalytic strategy is further highlighted by its successful application in the late-stage functionalization of biologically active skeletons.

Graphical abstract: Photocatalytic dehydrogenative oxidation/amination of 2-alkyl benzamides under transition-metal-free conditions
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