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Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.

ABSTRACT: We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.

SUBMITTER: Maity P

PROVIDER: S-EPMC4215808 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.

Maity Prantik P Shacklady-McAtee Danielle M DM Yap Glenn P A GP Sirianni Eric R ER Watson Mary P MP

Journal of the American Chemical Society 20121226 1

We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines. ...[more]

PMID: 23268734

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