Intramolecular Photochemical Cross‐Coupling Reactions of 3‐Acyl‐2‐haloindoles and 2‐Chloropyrrole‐3‐carbaldehydes with Substituted Benzenes
Authors:
- 24 November 2009
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 351 (17) , 2839-2844
Abstract
Highly efficient syntheses of indolo[2,1‐a]isoquinolines, indolo[2,1‐a][2]benzazepines, pyrrolo[2,1‐a]isoquinolines and pyrrolo[1,2‐a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross‐coupling reactions of 3‐acyl‐2‐halo‐N‐(ω‐arylalkyl)indoles and 2‐chloro‐N‐(ω‐arylalkyl)pyrrole‐3‐carbaldehydes in acetone. A new heterocyclic ring system – pyrrolo[1,2‐d][1,4]benzoxazepine – has also been constructed for the first time in this work by the photocyclization of 2‐chloro‐N‐(2‐phenoxyethyl)pyrrole‐3‐carbaldehyde.Keywords
This publication has 54 references indexed in Scilit:
- Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine LigandsAccounts of Chemical Research, 2008
- Synthesis of the CD-ring of the anticancer agent streptonigrin: studies of aryl–aryl coupling methodologiesTetrahedron, 2006
- Selected Patented Cross-Coupling Reaction TechnologiesChemical Reviews, 2006
- On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical ReviewAdvanced Synthesis & Catalysis, 2006
- Application of a catalytic palladium biaryl synthesis reaction, via C–H functionalization, to the total synthesis of Amaryllidaceae alkaloidsTetrahedron, 2004
- Transition Metal‐Catalyzed Carbon−Carbon Bond Formation with Grignard Reagents − Novel Reactions with a Classic ReagentEuropean Journal of Organic Chemistry, 2004
- Application of cross-coupling reactions in MerckJournal of Organometallic Chemistry, 2002
- The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product SynthesisAngewandte Chemie International Edition, 2001
- DieB-Alkyl-Suzuki-Miyaura-Kreuzkupplung: Entwicklung, Untersuchungen zum Mechanismus und Anwendungen in der NaturstoffsyntheseAngewandte Chemie, 2001
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995