Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.
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.
Tsvelikhovsky
Dmitry
D
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D000166:Acridines / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002227:Carbazoles / Q000737:chemistry*; D003500:Cyclization; D003984:Dibenzazepines / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008024:Ligands; D010165:Palladium / Q000737:chemistry*
D000166:Acridines; D000814:Aniline Compounds; D002227:Carbazoles; D003984:Dibenzazepines; D006571:Heterocyclic Compounds; D007211:Indoles; D008024:Ligands; D010165:Palladium; C025257:2-chloroaniline