Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate

Abstract

Carbonate. -In comparison with reported procedures for sulfenylation of indoles (I), the present method is not moisture sensitive and carried out in the green solvent dimethyl carbonate. It is noteworthy that both of the sulfenyl groups of a symmetric disulfide (II) take part in the reaction.

A novel and one-pot method for synthesis of unprecedented 3,3-dimethyl-2-amide indoles under metal-free conditions

“…c o m / l o c a t e / t e t l e t screening of the amount of iodine at 100°C, it was found that 5.0 equiv of iodine was the promising amount in both terms of reactivity and conversion rate (Table 1, entry 6 and 7). To improve the yields of 2-amide indoles, the reaction conditions were further optimized by adjusting several parameters, including substrate concentration (Table 1, entries 8-10) and solvent (Table 1, entries [11][12][13][14]. Several solvents were explored to examine the feasibility of the reaction, but no desired product was found.…”

A Novel Approach to Access Aryl Iodides and Disulfides via Dehydrazination of Arylhydrazines and Arylsulfonylhydrazides

“…Firstly, I 2 promoted the successive removal of hydrogen and oxygen from 1 and leads to the synthesis of intermediate 5 with the removal of HI and HOI which subsequently provide molecular iodine for the catalytic cycle. The removal of molecular nitrogen from 5 , gave sulfenyliodide 6 . Intermediate 5 and 6 condensed together to provide the desired disulfide 9 with the extrusion of I 2 and N 2 .…”

Metal‐Free Oxidative Carbon‐Heteroatom Bond Formation Through C–H Bond Functionalization

“…Wei and co‐workers developed efficient C(sp 2 )‐sulfenylation of indoles 202 under ambient conditions (Scheme ) 94. Various N ‐protected and unprotected indoles 202 were oxidatively sulfenylated by treatment with disulfides in the presence of catalytic iodine and DMSO, giving 3‐sulfenylindoles 203 in excellent yields.…”