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

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

doi:10.1039/C8SC04134B

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Download options Please wait...

Supplementary files

Supplementary information PDF (6319K)

Article information

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

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

Download Citation

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

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Science