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Synfacts 2011(1): 0075-0075
DOI: 10.1055/s-0030-1259114
DOI: 10.1055/s-0030-1259114
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Pd-Ligand Controlled Cyclization for the Preparation of Heteroaromatics
Rezensent(en):Paul Knochel, Andreas K. SteibD. Tsvelikhovsky, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines
J. Am. Chem. Soc. 2010, 132: 14048-14051
Massachusetts Institute of Technology, Cambridge, USA
Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines
J. Am. Chem. Soc. 2010, 132: 14048-14051
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2010 (online)
Key words
heterocycles - cyclization - carbazoles - indoles - dibenzazepines - acridines - palladium
Significance
Various vinyl diphenylamine intermediates are selectively cyclized to the corresponding five-, six- or seven-membered heteroaromatics. The regioselectivity of these palladium-catalyzed cyclizations is almost exclusively directed by the used ligand.
Comment
By using 2-bromostyrene and 2-chloroaniline derivatives in this palladium-catalyzed reaction with DavePhos as ligand, a direct one-pot synthesis was achieved, furnishing 5H-diazepines in good to excellent yields.