Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane-Disulfide Interchange Reaction

Takumi Nakajima; Ken Takano; Hiromu Maeda; Yohei Ogiwara; Norio Sakai

doi:10.1002/asia.202101101

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane-Disulfide Interchange Reaction

Chem Asian J. 2021 Dec 13;16(24):4103-4107. doi: 10.1002/asia.202101101. Epub 2021 Nov 5.

Authors

Takumi Nakajima¹, Ken Takano¹, Hiromu Maeda¹, Yohei Ogiwara¹, Norio Sakai¹

Affiliation

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba, 278-8510, Japan.

PMID: 34693645
DOI: 10.1002/asia.202101101

Abstract

The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur-sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.

Keywords: alkyl carboxylate; carbon-sulfur bond formation; disilathiane; disulfide; sulfur-sulfur bond cleavage.