One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

Abstract

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was achieved for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. Key features are the successful integration of a copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, a rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3H bond of indoles, and a reduction of the resultant enamides to tryptamine derivatives