Catalytic Cross-Coupling of Unactivated Arenes

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-acet...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2007-05, Vol.316 (5828), p.1172-1175
Main Authors: Stuart, David R, Fagnou, Keith
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzene
Benzene - chemistry
Catalysis
Catalysts
Cesium
Chemical synthesis
Chemistry
Cross coupling
Design engineering
Electropositivity
Exact sciences and technology
General and physical chemistry
Halides
Hydrocarbons, Aromatic - chemistry
Indoles
Indoles - chemistry
Joining
Microwaves
Molecules
Organic chemistry
Palladium
Palladium - chemistry
Protons
Reactivity
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary: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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.1141956