Practical synthesis of unsymmetrical disulfides promoted by bromodimethylsulfonium bromide

Abstract

Oxidative cross-coupling of two thiols is the most direct tool for the synthesis of unsymmetrical disulfides and highly desirable across academia and industry. However, the inevitable formation of significant amount...

Metal‐Free and NBS‐Mediated Direct Thiol‐Disulfide Exchange Reaction to Access Unsymmetrical Disulfides

“…Based on previous reports and control experiments, a plausible mechanism was proposed in Scheme 6 [6a,16,19–21] . The initial reaction between BnSH ( 1 a ) and NBS provides the sulfenyl bromide A and succinimide ( 5 ).…”

1,2-Fluorosulfenylation of unactivated alkenes with thiols and a fluoride source promoted by bromodimethylsulfonium bromide

“…On that basis we successfully performed the practical synthesis of unsymmetrical disulfides by using BDMS as the promotor. 12 In the continuation of our project for the synthesis of sulfur-containing compounds, 13 we envision that the high reactivity and excellent selectivity of BDMS toward thiols would allow the multicomponent fluorosulfenylation of alkenes, through the formation of sulfenyl bromides, thiiranium ions and nucleophilic (F − ) ring opening addition 5 successively (Scheme 1C). This strategy offers a new route toward the synthesis of β-fluorinated thioethers that could directly use thiols and unactivated alkenes.…”