Methanesulfenylation of mercaptans and β-dicarbonyls with DMSO

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.