Issue 9, 2023

Metal-free photoinduced hydrogen atom transfer assisted C(sp3)–H thioarylation

Abstract

C−H thioarylation of hydrocarbon building blocks is a highly desirable synthetic transformation because of its prevalence in various pharmaceuticals and organic functional materials. However, to date all the developments majorly rely on peroxide mediated transformations. Unfortunately, the harsh reaction conditions of these reactions cause severe functional group intolerance. To overcome these issues, photo-induced radical coupling reactions have gained significant attention as a sustainable solution, which require either metal based photosensitizers or the use of an organophotocatalyst. Herein, we demonstrate a mild metal-free approach for C(sp3)–H thioarylation using thioxanthone as a photo-catalyst. The protocol is compatible with various arenes, as well as unactivated alkanes and cycloalkanes. The post-synthetic modifications of thioarylated compounds are also demonstrated through cross-coupling reactions and functional group interconversions.

Graphical abstract: Metal-free photoinduced hydrogen atom transfer assisted C(sp3)–H thioarylation

Supplementary files

Article information

Article type
Communication
Submitted
31 1月 2023
Accepted
30 3月 2023
First published
30 3月 2023

Green Chem., 2023,25, 3431-3436

Metal-free photoinduced hydrogen atom transfer assisted C(sp3)–H thioarylation

J. Grover, G. Prakash, C. Teja, G. K. Lahiri and D. Maiti, Green Chem., 2023, 25, 3431 DOI: 10.1039/D3GC00359K

To request permission to reproduce material from this article, 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 publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements