Regiocontrolled Wacker Oxidation of Cinnamyl Azides

Angela S. Carlson; Cristian Calcanas; Ryan M. Brunner; Joseph J. Topczewski

doi:10.1021/acs.orglett.8b00344

Regiocontrolled Wacker Oxidation of Cinnamyl Azides

Angela S. Carlson, Cristian Calcanas, Ryan M. Brunner, Joseph J. Topczewski

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

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 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.

Original language	English (US)
Pages (from-to)	1604-1607
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00344
State	Published - Mar 16 2018

Bibliographical note

Funding Information:
Financial support was provided by the University of Minnesota and The American Chemical Society’s Petroleum Research Fund (PRF No. 56505-DNI1). This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718. We also acknowledge NIH Shared Instrumentation Grant No. S10OD011952.

Publisher Copyright:
© 2018 American Chemical Society.

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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 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.",

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Regiocontrolled Wacker Oxidation of Cinnamyl Azides

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