The Catalytic Cross-Coupling of Unactivated Arenes
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- 25 May 2007
- journal article
- other
- Published by American Association for the Advancement of Science (AAAS) in Science
- Vol. 316 (5828) , 1172-1175
- https://doi.org/10.1126/science.1141956
Abstract
The industrially important coupling of aromatic compounds has generally required differential prefunctionalization of the arene coupling partners with a halide and an electropositive group. Here we report that palladium, in conjunction with a copper oxidant, can catalyze the cross-coupling of N-acetylindoles and benzenes in high yield and high regioselectivity across a range of indoles without recourse to activating groups. These reactions are completely selective for arene cross-coupling, with no products arising from indole or benzene homo-coupling detected by spectroscopic analysis. This efficient reactivity should be useful in the design of other oxidative arene cross-couplings as well.Keywords
This publication has 17 references indexed in Scilit:
- Aryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct ArylationChemical Reviews, 2007
- Intermolecular Cross-Coupling of Simple Arenes via C−H Activation by Tuning Concentrations of Arenes and TFAOrganometallics, 2006
- Synthesis of Biaryls via Catalytic Decarboxylative CouplingScience, 2006
- Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined OligothiophenesJournal of the American Chemical Society, 2006
- Catalytic Intermolecular Direct Arylation of PerfluorobenzenesJournal of the American Chemical Society, 2006
- Direct Palladium-Catalyzed C-2 and C-3 Arylation of Indoles: A Mechanistic Rationale for RegioselectivityJournal of the American Chemical Society, 2005
- Enantioselective Oxidative Biaryl Coupling Reactions Catalyzed by 1,5-Diazadecalin Metal Complexes: Efficient Formation of Chiral Functionalized BINOL DerivativesThe Journal of Organic Chemistry, 2003
- Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann ReactionChemical Reviews, 2002
- Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective trans-Hydroarylation of Alkynes by Simple ArenesJournal of the American Chemical Society, 2000
- Synthesis of enantiomerically pure 2,2'-dihydroxy-1,1'-binaphthyl, 2,2'-diamino-1,1'-binaphthyl, and 2-amino-2'-hydroxy-1,1'-binaphthyl. Comparison of processes operating as diastereoselective crystallization and as second order asymmetric transformationThe Journal of Organic Chemistry, 1992