Kannika La-OngthongPhiphop NaweephattanaOnnicha KhaikatePanida SurawatanawongDarunee SoorukramManat PohmakotrVichai ReutrakulPawaret LeowanawatChutima KuhakarnMahidol University2020-08-252020-08-252020-05-15Journal of Organic Chemistry. Vol.85, No.10 (2020), 6338-635115206904002232632-s2.0-85087946538https://repository.li.mahidol.ac.th/handle/20.500.14594/57811Copyright © 2020 American Chemical Society. Reactions of o-alkynylisocyanobenzenes with a variety of alkanethiols (Alk-SH) provide the corresponding bis-thiolated indole derivatives. The advantages of the reaction include metal-free, room-temperature, mild reaction conditions and broad functional group compatibility. The reaction proceeds via nucleophilic addition of an alkanethiol to an isonitrile moiety, 5-exo cyclization, followed by nucleophilic addition of an alkanethiol to a 3-alkylidene indole intermediate. Density functional calculations on the electronic structures and relative free energies of 5-exo and 6-endo cyclization pathways support that the 5-exo cyclization is preferable.Mahidol UniversityChemistryArticleSCOPUS10.1021/acs.joc.0c00003