Jatuporn MeesinManat PohmakotrVichai ReutrakulDarunee SoorukramPawaret LeowanawatChutima KuhakarnMahidol University2018-12-212019-03-142018-12-212019-03-142017-01-01Organic and Biomolecular Chemistry. Vol.15, No.17 (2017), 3662-3669147705202-s2.0-85021673690https://repository.li.mahidol.ac.th/handle/20.500.14594/42050© The Royal Society of Chemistry 2017. An efficient and metal-free approach to N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines has been developed. In the presence of iodine and tert-butylhydroperoxide (TBHP), a variety of 2-alkynyl-N,N-dialkylanilines underwent a cascade radical annulation to yield 3-arylsulfonylindoles. In contrast, 3-arylsulfanylindoles were conveniently prepared by iodine mediated electrophilic annulation reactions. The present protocol uses the economical and environmentally friendly I2-TBHP or I2system, and potentially bioactive N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles with various functional groups were successfully synthesized in moderate to good yields.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1039/c7ob00366h