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Rh(I)-catalyzed direct arylation of azines.

ABSTRACT: The Rh(I)-catalyzed direct arylation of azines has been developed. Quinolines and 2-substituted pyridines couple with aryl bromides to efficiently afford ortho-arylated azine products using the commercially available and air-stable catalyst [RhCl(CO)2]2. Electron-deficient and electron-rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether, and ketone functionalities are compatible with the reaction conditions. Aroyl chlorides also serve as effective azine coupling partners to give ortho-arylation products via a decarbonylation pathway.

SUBMITTER: Berman AM

PROVIDER: S-EPMC3112309 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Rh(I)-catalyzed direct arylation of azines.

Berman Ashley M AM Bergman Robert G RG Ellman Jonathan A JA

The Journal of organic chemistry 20101029 22

The Rh(I)-catalyzed direct arylation of azines has been developed. Quinolines and 2-substituted pyridines couple with aryl bromides to efficiently afford ortho-arylated azine products using the commercially available and air-stable catalyst [RhCl(CO)2]2. Electron-deficient and electron-rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether, and ketone functionalities are compatible with the reaction conditions. Aroyl chlorides also serve as effective a ...[more]

PMID: 21033740

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