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Updated: Jun 4, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 +
Shu Wang1,2, Ge Liang1,2, Cheng Wang1,2
1Key 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.
Abstract:
Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-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(sp3)-H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).
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