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

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      Publication Details (including relevant citation   information):

      J. Am. Chem. Soc.,  2010, 132 (40), pp 14048–14051

      Publication Date (Web): September 21, 2010   (Communication)

      DOI: 10.1021/ja107511g

      Abstract:

      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.

      Address (URL): http://pubs.acs.org/doi/pdf/10.1021/ja107511g