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Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

ABSTRACT: A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 ?-azido ketones were isolated (25-92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily diversified.

SUBMITTER: Carlson AS

PROVIDER: S-EPMC5989718 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

Carlson Angela S AS Calcanas Cristian C Brunner Ryan M RM Topczewski Joseph J JJ

Organic letters 20180302 6

A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25-92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily diversified. ...[more]

PMID: 29498865

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