Photoredox-mediated remote C(sp3)–H heteroarylation of free alcohols

Guo-Xing Li; Xiafei Hu; Gang He; Gong Chen

doi:10.1039/C8SC04134B

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Photoredox-mediated remote C(sp³)–H heteroarylation of free alcohols†

Guo-Xing Li,^a Xiafei Hu,^a Gang He*^a and Gong Chen

*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China
E-mail: gongchen@nankai.edu.cn

^b Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, USA
E-mail: guc11@psu.edu

Abstract

We report an efficient and economical method for remote δ C(sp³)–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C–C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.

This article is part of the themed collections: Celebrating 100 Years of Chemistry at Nankai University, Most popular 2019-2020 organic chemistry articles, Most popular 2018-2019 organic chemistry articles, Editor's choice - Paolo Melchiorre and 2018 Chemical Science HOT Article Collection

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Article information

DOI: https://doi.org/10.1039/C8SC04134B
Article type: Edge Article
Submitted: 17 Sept. 2018
Accepted: 27 Okt. 2018
First published: 30 Okt. 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 688-693

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Photoredox-mediated remote C(sp³)–H heteroarylation of free alcohols

G. Li, X. Hu, G. He and G. Chen, Chem. Sci., 2019, 10, 688 DOI: 10.1039/C8SC04134B

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