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

Zhao Wei, Zhiqin He, Xiaohui Yang, Yang Yu, Jonathan B. Baell, Fei Huang

2023The Journal of Organic Chemistry16 citationsDOI

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.

Topics & Concepts

AlkylCatalysisChemistryOrganic chemistryPhotochemistrySynthesis of Organic CompoundsOxidative Organic Chemistry ReactionsRadical Photochemical Reactions
Visible-Light-Induced Synthesis of 3-Alkyl Chromones under Catalyst- and Additive-Free Conditions | Litcius