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A general method for copper-catalyzed arene cross-dimerization.

ABSTRACT: A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contrast to existing methodology that often employs a large excess of one of the arenes. Common functionalities such as ester, ketone, aldehyde, ether, nitrile, nitro, and amine are well-tolerated.

SUBMITTER: Do HQ

PROVIDER: S-EPMC3168561 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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A general method for copper-catalyzed arene cross-dimerization.

Do Hien-Quang HQ Daugulis Olafs O

Journal of the American Chemical Society 20110808 34

A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contras ...[more]

PMID: 21823581

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