Visible-Light-Induced -Quinone Methides Formation in Situ Using -Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction.

Org Lett

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, P. R. China.

Published: December 2024

Reported herein is the generation of -quinone methides (-QMs) via metal-free visible-light-induced oxidation of -alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp)-H bond of -alkylarenols via single electron transfer (SET) and the formation of -QMs via hydrogen atom transfer (HAT).

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http://dx.doi.org/10.1021/acs.orglett.4c04494DOI Listing

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