A General Method for Copper-Catalyzed Arylation of Arene C−H Bonds
Top Cited Papers
- 15 October 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (45) , 15185-15192
- https://doi.org/10.1021/ja805688p
Abstract
A general method for copper-catalyzed arylation of sp2 C−H bonds with pKaʼs below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper−phenanthroline complex intermediates were independently synthesized.Keywords
This publication has 77 references indexed in Scilit:
- Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond ActivationAccounts of Chemical Research, 2008
- Copper Complexes of Anionic Nitrogen Ligands in the Amidation and Imidation of Aryl HalidesJournal of the American Chemical Society, 2008
- Twofold C−H Functionalization: Palladium-Catalyzed Ortho Arylation of AnilidesOrganic Letters, 2008
- Enamide Synthesis by Copper‐Catalyzed Cross‐Coupling of Amides and Potassium Alkenyltrifluoroborate SaltsAngewandte Chemie International Edition in English, 2008
- Copper-Catalyzed Arylation and Alkenylation of Polyfluoroarene C−H BondsJournal of the American Chemical Society, 2008
- C−C Bond Formation via Double C−H Functionalization: Aerobic Oxidative Coupling as a Method for Synthesizing Heterocoupled BiarylsOrganic Letters, 2007
- Direct transition metal-catalyzed functionalization of heteroaromatic compoundsChemical Society Reviews, 2007
- Highly Efficient Route to Fused Polycyclic Aromatics via Palladium-Catalyzed Aryne Annulation by Aryl HalidesThe Journal of Organic Chemistry, 2006
- Synthesis of Highly Substituted Pyridazines through Alkynyl Boronic Ester Cycloaddition ReactionsAngewandte Chemie International Edition in English, 2005
- Chromatographic and Spectral Characteristics of Some PolythienylsJournal of the American Chemical Society, 1947