Methanesulfenylation of mercaptans and β-dicarbonyls with DMSO

Abstract

The methanesulfenylation of various mercaptans and β-dicarbonyls has been investigated using in-situ generated methyl methanethiosulfonate (MMTS) from DMSO, facilitated by a catalytic amount of (COCl)₂. Employing the MMTS solution alongside Et₃N led to the synthesis of a range of unsymmetrical disulfides with good yields. Furthermore, the introduction of [²H₆]-DMSO enabled the successful preparation of various [²H₃]-disulfides. In the case of most β-dicarbonyls, successful methanesulfenylation was accomplished using Et₃N and DBU, resulting in favorable yields.

GRAPHICAL ABSTRACT

KEYWORDS:

• Methanesulfenylation
• β-dicarbonyls
• mercaptans
• methyl methanethioslfonate
• dimethyl sulfoxide

Acknowledgment

We gratefully acknowledge support by the National Natural Science Foundation of China (No. 32130083).

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the National Natural Science Foundation of China: [Grant Number No. 32130083].