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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Author(s)
Tsvelikhovsky, Dmitry
Buchwald, Stephen Leffler
Date Issued
September 2010
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Tsvelikhovsky, Dmitry, and Stephen L. Buchwald. “Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines.” Journal of the American Chemical Society 132.40 (2010): 14048–14051.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja107511g
