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Visible-Light-Enhanced Ring Opening of Cycloalkanols Enabled by Brønsted Base-Tethered Acyloxy Radical Induced Hydrogen Atom Transfer-Electron Transfer

Rong Zhao, Yuan Yao, Dan Zhu, Denghu Chang, Yang Liu and Lei Shi*

*Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, P. R. China, Email: lshihit.edu.cn

R. Zhao, Y. Yao, D. Zhu, D. Chang, Y. Liu, L. Shi, Org. Lett., 2018, 20, 1228-1231.

DOI: 10.1021/acs.orglett.8b00161 (free Supporting Information)


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Abstract

A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, provides diverse γ, δ, and even more remotely halogenated ketones in good yields under mild conditions.

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proposed mechanism



Key Words

bromination, iodination, phthaloyl peroxide, photochemistry


ID: J54-Y2018