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A metal-free divergent synthesis of indole compounds dependent on a reagent via intramolecular C(sp2)–H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl2 at 70 °C was found to give 2-thiomethylindoles, while replacing DMSO with diethyl sulfoxide afforded 2-unsubstituted indoles in a highly selective manner.

Graphical abstract: Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl2 and dimethyl/diethyl sulfoxides

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