Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines
- 21 September 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (40), 14048-14051
- https://doi.org/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.Keywords
This publication has 32 references indexed in Scilit:
- Synthesis of Acridines by the [4 + 2] Annulation of Arynes and 2-Aminoaryl KetonesThe Journal of Organic Chemistry, 2010
- A Tandem Cascade Cyclization−Electrophilic Aromatic Substitution: Application in the Total Synthesis of (+)-AngelichalconeJournal of the American Chemical Society, 2009
- A New Industrial Process for 10-Methoxyiminostilbene: Key Intermediate for the Synthesis of OxcarbazepineOrganic Process Research & Development, 2009
- A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl ChloridesJournal of the American Chemical Society, 2008
- Biaryl Phosphane Ligands in Palladium‐Catalyzed AminationAngewandte Chemie-International Edition, 2008
- Synthesis of Heterocycles via Palladium-Catalyzed Oxidative Addition (Chem. Rev. 2006, 106, 4644−4680. Published on the Web October 11, 2006.)Chemical Reviews, 2006
- Combined C−H Functionalization/C−N Bond Formation Route to CarbazolesJournal of the American Chemical Society, 2005
- Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and MechanismAngewandte Chemie-International Edition, 1998
- Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approaches to ergot alkaloidsThe Journal of Organic Chemistry, 1984
- Dibenz[b,f]azepines and related ring systemsChemical Reviews, 1974