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Science 20 March 2009:
Vol. 323. no. 5921, pp. 1593 - 1597
DOI: 10.1126/science.1169975
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Reports

A Meta-Selective Copper-Catalyzed C–H Bond Arylation

Robert J. Phipps and Matthew J. Gaunt*

For over a century, chemical transformations of benzene derivatives have been guided by the high selectivity for electrophilic attack at the ortho/para positions in electron-rich substrates and at the meta position in electron-deficient molecules. We have developed a copper-catalyzed arylation reaction that, in contrast, selectively substitutes phenyl electrophiles at the aromatic carbon–hydrogen sites meta to an amido substituent. This previously elusive class of transformation is applicable to a broad range of aromatic compounds.

Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.

* To whom correspondence should be addressed. E-mail: mjg32{at}cam.ac.uk

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Science. ISSN 0036-8075 (print), 1095-9203 (online)