Issue 10, 2017

A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

Abstract

We report a unified photoredox-catalysis strategy for both hydroxylation and amidation of tertiary and benzylic C–H bonds. Use of hydroxyl perfluorobenziodoxole (PFBl–OH) oxidant is critical for efficient tertiary C–H functionalization, likely due to the enhanced electrophilicity of the benziodoxole radical. Benzylic methylene C–H bonds can be hydroxylated or amidated using unmodified hydroxyl benziodoxole oxidant Bl–OH under similar conditions. An ionic mechanism involving nucleophilic trapping of a carbocation intermediate by H2O or CH3CN cosolvent is presented.

Graphical abstract: A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

Supplementary files

Article information

Article type
Edge Article
Submitted
21 6月 2017
Accepted
02 9月 2017
First published
04 9月 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 7180-7185

A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine

G. Li, C. A. Morales-Rivera, F. Gao, Y. Wang, G. He, P. Liu and G. Chen, Chem. Sci., 2017, 8, 7180 DOI: 10.1039/C7SC02773G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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