Visible-Light-Induced Oxidative Generation of o-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition Reactions

Author:

Tanaka Kenta1,Hoshino Yujiro2,Nohara Shoya2,Iwai Suguru2,Yamaguchi Naoya2,Asada Yosuke2,Kamiyama Yusuke2,Tanaka Yuta2

Affiliation:

1. Research Institute for Interdisciplinary Science, Okayama University

2. Graduate School of Environment and Information Sciences, Yokohama National University

Abstract

AbstractOrganophotoredox-catalyzed oxidative generation of o-quinone methides (o-QMs) for inverse-electron-demand [4+2] cycloaddition reactions has been developed. One-electron oxidation of 2-(sulfanylmethyl)phenols by thioxanthylium photoredox catalyst generated o-QMs, which reacted with various styrenes to produce chromanes with high regioselectivity. This reaction offers a valuable approach for in situ generating o-QMs via one-electron oxidation process under irradiation with mild green light.

Funder

Tokuyama Science Foundation

Takahashi Industrial and Economic Research Foundation

Research Foundation for the Electrotechnology of Chubu

Futaba Electronics Memorial Foundation

Yashima Environment Technology Foundation

Naohiko Fukuoka Memorial Foundation

Japan Society for Bioscience, Biotechnology, and Agrochemistry

Society of Iodine Science

Japan Society for the Promotion of Science

Yokohama National University

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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