Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

Ting Liu; Renhua Qiu; Longzhi Zhu; Shuang-Feng Yin; Chak-Tong Au; Nobuaki Kambe

doi:10.1002/asia.201801679

Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

Chem Asian J. 2018 Dec 18;13(24):3833-3837. doi: 10.1002/asia.201801679. Epub 2018 Nov 27.

Authors

Ting Liu¹, Renhua Qiu^{1

2}, Longzhi Zhu¹, Shuang-Feng Yin¹, Chak-Tong Au³, Nobuaki Kambe^{1

2}

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410081, Hunan Province, China.
² Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
³ College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan, Hunan, China.

PMID: 30444061
DOI: 10.1002/asia.201801679

Abstract

A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.

Keywords: alkyl halides; alkyl sulfides; metal-free; transalkylation.

Abstract

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