Issue 12, 2019

Recent advances in photocatalytic C–S/P–S bond formation via the generation of sulfur centered radicals and functionalization

Abstract

Thioyl and sulfonyl radicals are usually produced from various thiols and sulfonyl derivatives in high efficiency by single-electron-transfer (SET) oxidation. The generated sulfur (thioyl/sulfonyl) radicals are also highly reactive intermediates having various applications in the construction of organosulfur compounds in the field of organic synthesis. Recently, photoredox-catalyzed C–S/P–S bond formation via the generation of sulfur centered radicals has been studied extensively. In the photoredox catalytic process, a variety of S–H, S–S, S–C, S–N, and S–X (F, Cl, Br, I) bonds, and even active sulfone-containing skeletons can be easily transformed into the corresponding thioyl/sulfonyl radicals. Some of these transformations are achieved by a combination of photoredox catalysts (i.e., TiO2, Bi2O3, eosin Y, fac-[Ir(ppy)3], [Ru(bpy)3]2+) and other catalysts such as strong bases, Lewis acids, organocatalysts and transition metal catalysts. Compared with previous methods, photoredox catalysis is inexpensive and features the advantages of high efficiency and easy utilization in addition to being environmentally-benign. In this review, we have focused on the research on photoredox-catalyzed C–S/P–S bond formation via the generation of thioyl/sulfonyl radicals and further functionalization in the past few years. We hope to offer chemists the tools to open the door for further progress in organsulfur chemistry.

Graphical abstract: Recent advances in photocatalytic C–S/P–S bond formation via the generation of sulfur centered radicals and functionalization

Article information

Article type
Review Article
Submitted
14 Dec. 2018
Accepted
30 Janv. 2019
First published
31 Janv. 2019

Org. Chem. Front., 2019,6, 2048-2066

Recent advances in photocatalytic C–S/P–S bond formation via the generation of sulfur centered radicals and functionalization

W. Guo, K. Tao, W. Tan, M. Zhao, L. Zheng and X. Fan, Org. Chem. Front., 2019, 6, 2048 DOI: 10.1039/C8QO01353E

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