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The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor.

journal of the american chemical society

Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-<i>N</i>-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines

Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines