One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal–Knorr synthesis of pyrrole derivatives catalyzed by TCCA

Efficient electrosynthesis of sulfinic esters via oxidative cross‐coupling between alcohols and thiophenols

“…Based on the above results and the previous reports, a plausible mechanism for this electorchemical oxidative cross‐coupling is proposed in Scheme . First, the sulfur radical was formed by the oxidation and deprotonation of 1a.…”

Strategies for the direct oxidative esterification of thiols with alcohols

“…In 2013, Hemmati and co-workers developed a two-step one-pot method for the preparation of sulfonic ester derivatives 43 from the respective thiols 41 and alcohols 42 through oxidative chlorination of thiols to sulfonyl chlorides in the presence of trichloroisocyanuric acid (TCCA), tetrabutylammonium chloride ( t Bu 4 NCl), and water followed by reaction with alcohols under basic conditions ( Scheme 19a ). 37 Although either aromatic and aliphatic derivatives of both starting materials exhibited good applications under standard conditions and provided the desired products in high to excellent yields, the toxicity of TCCA might limit the application profile of this synthetic strategy. Noteworthy, when disulfides were subjected to the reaction in place of thiols, the same set of sulfonic ester products were obtained in close yields.…”

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

“…Oxidative chlorination of thiols was frequently applied to synthetic pathways using several combinations of oxidants and chloride sources, i.e. NCS/Bu 4 NCl, 24 TCCA/BnMe 3 NCl, [25][26][27] chloramine-T/Bu 4 NCl, 28 DCH/BnMe 3 NCl, 29 33 NaOCl/HCl, 34 PCBS or TCBDA/BnMe 3 NCl, 35 nitrate salt with TMSCl 36 or sulfuryl chloride, 37 and oxone/KX. 38 In addition, the sole oxidants may play a dual role also as a source of chloride i.e.…”