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Science 25 May 2007:
Vol. 316. no. 5828, pp. 1172 - 1175
DOI: 10.1126/science.1141956
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Reports

The Catalytic Cross-Coupling of Unactivated Arenes

David R. Stuart and Keith Fagnou*

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.

Center for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.

* To whom correspondence should be addressed. E-mail: keith.fagnou{at}uottawa.ca

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THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
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R. J. Phipps and M. J. Gaunt (2009)
Science 323, 1593-1597
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Green chemistry for chemical synthesis.
C.-J. Li and B. M. Trost (2008)
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