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

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

doi:10.1039/c8sc04134b

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

Chem Sci. 2018 Oct 30;10(3):688-693. doi: 10.1039/c8sc04134b. eCollection 2019 Jan 21.

Authors

Guo-Xing Li¹, Xiafei Hu¹, Gang He¹, Gong Chen^{1

2}

Affiliations

¹ 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 . Email: gongchen@nankai.edu.cn.
² Department of Chemistry , The Pennsylvania State University , 104 Chemistry Building, University Park , PA 16802 , USA . Email: 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.