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 2023
Accepted
30 3 2023
First published
30 3 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

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