Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: Preparation of carbazoles, indoles, dibenzazepines, and acridines

Dmitry Tsvelikhovsky, Stephen L. Buchwald

Research output: Contribution to journalArticlepeer-review

181 Scopus citations

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.

Original languageAmerican English
Pages (from-to)14048-14051
Number of pages4
JournalJournal of the American Chemical Society
Volume132
Issue number40
DOIs
StatePublished - 13 Oct 2010
Externally publishedYes

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