Oxidative Coupling of Arylboronic Acids with Arenes via Rh-Catalyzed Direct C−H Arylation
- 12 December 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (1), 129-131
- https://doi.org/10.1021/ol702659a
Abstract
Oxidative coupling of three different arenes and a thiophene derivative with various arylboronic acids was achieved with a [RhCl(C2H4)2]2/P[p-(CF3)C6H4]3 catalyst system. Commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) was used as a stoichiometric oxidant. A 2-pyridyl group and an imine functional group served as ortho-directing groups to mediate the direct C−H arylation by a Rh complex. Moderate to excellent yields were obtained for the coupling reactions.Keywords
This publication has 35 references indexed in Scilit:
- The Catalytic Cross-Coupling of Unactivated ArenesScience, 2007
- Direct transition metal-catalyzed functionalization of heteroaromatic compoundsChemical Society Reviews, 2007
- Aryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct ArylationChemical Reviews, 2007
- Catalytic Direct Arylation of Heteroaromatic CompoundsChemistry Letters, 2006
- Atroposelective Synthesis of Axially Chiral Biaryl CompoundsAngewandte Chemie, 2005
- Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann ReactionChemical Reviews, 2002
- Merry-Go-Round Multiple Alkylation on Aromatic Rings via Rhodium CatalysisJournal of the American Chemical Society, 2000
- 1,1‘-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New MaterialsChemical Reviews, 1998
- Electroluminescent Conjugated Polymers—Seeing Polymers in a New LightAngewandte Chemie, 1998
- Conjugated poly(thiophenes): synthesis, functionalization, and applicationsChemical Reviews, 1992