Issue 3, 2019

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

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.

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

Supplementary files

Article information

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
Creative Commons BY-NC license

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

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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