Regiocontrolled Wacker Oxidation of Cinnamyl Azides

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

Research output: Contribution to journalArticlepeer-review

11 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 languageEnglish (US)
Pages (from-to)1604-1607
Number of pages4
JournalOrganic Letters
Volume20
Issue number6
DOIs
StatePublished - 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.

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