Visible-Light-Induced Synthesis of 3-Alkyl Chromones under Catalyst- and Additive-Free Conditions

J Org Chem. 2023 Oct 6;88(19):13634-13644. doi: 10.1021/acs.joc.3c01339. Epub 2023 Sep 7.

Abstract

Herein, we reported an efficient and facile visible-light-induced 3-alkyl chromone synthesis from easily accessible o-hydroxyaryl enaminones and α-diazo esters. In this protocol, excellent yields were obtained with a broad substrate scope at room temperature, tolerating various functional groups. Of note is that this eco-friendly methodology features catalyst- and additive-free, mild reaction conditions, simple operation procedure, and easy scale-up, which affords a convenient pathway for the preparation of 3-alkyl chromones. Experimental results and density functional theory (DFT) computation analyses confirm the participation of carbene species and active cyclopropane intermediate.