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

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Science  20 Mar 2009:
Vol. 323, Issue 5921, pp. 1593-1597
DOI: 10.1126/science.1169975

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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.

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