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A catalytic, Bronsted base strategy for intermolecular allylic C-H amination.

ABSTRACT: A Brønsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.

SUBMITTER: Reed SA

PROVIDER: S-EPMC2751613 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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A catalytic, Brønsted base strategy for intermolecular allylic C-H amination.

Reed Sean A SA Mazzotti Anthony R AR White M Christina MC

Journal of the American Chemical Society 20090801 33

A Brønsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products. ...[more]

PMID: 19645492

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