Issue 13, 2023

Applications of trisulfide radical anion S3˙ in organic synthesis

Abstract

The trisulfide radical anion S3˙ is well-known as the blue chromophore in ultramarines and it has a versatile role in materials chemistry, especially in the redox chemistry of alkali metal–sulfur batteries, electrochemistry, analytical chemistry and geochemistry. However, the applications of this unique sulfur reagent in organic chemistry have only been exploited in the last ten years. This versatile source of sulfur can be easily formed by reaction of elemental sulfur (S8) with nucleophilic bases or by oxidation of sulfide (S2−) in readily available alkali–metal salts. Recent findings have revealed that S3˙ has a multi-faceted role in a variety of organic reactions for the synthesis of organosulfur compounds with applications ranging from pharmaceuticals to organic semiconductors. In addition, S3˙ may serve as a catalyst in certain organic transformations such as C–C bond formation cross-coupling reactions. In this review, the synthetic and mechanistic aspects of the role of the trisulfur radical anion S3˙ in organic chemistry are discussed.

Graphical abstract: Applications of trisulfide radical anion S3˙− in organic synthesis

Article information

Article type
Review Article
Submitted
04 Apr 2023
Accepted
28 Mai 2023
First published
30 Mai 2023

Org. Chem. Front., 2023,10, 3378-3400

Applications of trisulfide radical anion S3˙ in organic synthesis

P. Song, W. Rao, T. Chivers and S. Wang, Org. Chem. Front., 2023, 10, 3378 DOI: 10.1039/D3QO00496A

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