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A facile and efficient approach to 1,2-disubstituted indoles has been developed using a novel Cu(I)-catalyzed cascade coupling/cyclization reaction of 2-alkynylanilines with aryl iodides. Facilitated by CuI/t-BuOK without any ligand or CuI/Cs2CO3/1,10-phenanthroline, a variety of 1,2-disubstituted indoles were conveniently generated in one pot with good to excellent yields. Furthermore, a series of indolo[1,2-f]phenanthridines were successfully assembled from the tandem reactions of 2-alkynylanilines with o-dihaloarenes through copper-catalyzed coupling / cyclization followed by palladium-catalyzed intramolecular direct C(sp)-H arylation.

A practical Cu(I)-catalyzed domino approach to 1,2-disubstituted indoles and its application for the assembly of indolophenanthridines