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Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

ABSTRACT: We report the palladium-catalyzed oxidation of hindered alkenes to form linear allylic esters. The combination of palladium(II) benzoate, 4,5-diazafluoren-9-one, and benzoquinone catalyzes the mild oxidation of terminal alkenes with tert-butyl benzoyl peroxide as an oxidant in the presence of diverse functional groups. Selective oxidation of terminal alkenes in the presence of trisubstituted and disubstituted alkenes has been achieved, and the ability to conduct the reaction on a gram scale has been demonstrated. The mild conditions and high tolerance for auxiliary functionality make this method suitable for the synthesis and derivatization of complex molecules.

SUBMITTER: Litman ZC

PROVIDER: S-EPMC5999342 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

Litman Zachary C ZC Sharma Ankit A Hartwig John F JF

ACS catalysis 20170130 3

We report the palladium-catalyzed oxidation of hindered alkenes to form linear allylic esters. The combination of palladium(II) benzoate, 4,5-diazafluoren-9-one, and benzoquinone catalyzes the mild oxidation of terminal alkenes with <i>tert</i>-butyl benzoyl peroxide as an oxidant in the presence of diverse functional groups. Selective oxidation of terminal alkenes in the presence of trisubstituted and disubstituted alkenes has been achieved, and the ability to conduct the reaction on a gram sca ...[more]

PMID: 29910970

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