Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs)
Authors:
- 29 October 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 79 (22) , 11246-11253
Abstract
A direct and facile palladium-catalyzed C–H bond oxidative carbonylation reaction and oxidative cyclization for the synthesis of polycyclic aromatic hydrocarbons (PAHs) is reported herein. The intramolecular cyclocarbonylation, through C–H activation and C–C, C–O bond formations under mild conditions, proceeds smoothly with good functional group tolerance in high to excellent yields. The intramolecular palladium-catalyzed direct oxidative C–H bond functionalization for the C–O bond formation is also demonstrated, which provides an efficient approach for the construction of various PAHs.Keywords
Funding Information
- Ministry of Education of the People's Republic of China (2014ZP0004, 2014ZZ0046)
- Ministry of Science and Technology of the People's Republic of China (2011CB808600)
- National Natural Science Foundation of China (21172076, 21202046)
- Natural Science Foundation of Guangdong Province (10351064101000000)
This publication has 70 references indexed in Scilit:
- Synthesis of phenanthridinones viapalladium-catalyzed C(sp2)–H aminocarbonylation of unprotected o-arylanilinesChemical Communications, 2012
- Palladium‐Catalyzed Oxidative Double C-H Functionalization/Carbonylation for the Synthesis of XanthonesAngewandte Chemie International Edition, 2012
- Weak Coordination as a Powerful Means for Developing Broadly Useful C–H Functionalization ReactionsAccounts of Chemical Research, 2011
- Palladium-catalyzed carbonylative coupling reactions between Ar–X and carbon nucleophilesChemical Society Reviews, 2011
- Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formationChemical Society Reviews, 2011
- Pd(II)-Catalyzed Carbonylation of C(sp3)−H Bonds: A New Entry to 1,4-Dicarbonyl CompoundsJournal of the American Chemical Society, 2010
- Palladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsChemical Reviews, 2010
- Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond ActivationChemical Reviews, 2009
- Room‐Temperature Palladium‐Catalyzed C-H Activation: ortho‐Carbonylation of Aniline DerivativesAngewandte Chemie International Edition, 2009
- Palladium-Catalyzed Method for the Synthesis of Carbazoles via Tandem C−H Functionalization and C−N Bond FormationThe Journal of Organic Chemistry, 2008