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Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.

ABSTRACT: Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

SUBMITTER: Howell JM 

PROVIDER: S-EPMC4924472 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.

Howell Jennifer M JM   Feng Kaibo K   Clark Joseph R JR   Trzepkowski Louis J LJ   White M Christina MC  

Journal of the American Chemical Society 20151113 46

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization. ...[more]

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