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Issue 11, 2012
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Nitrate as a redox co-catalyst for the aerobic Pd-catalyzed oxidation of unactivated sp3-C–H bonds

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Abstract

This paper describes a new method for the catalytic aerobic oxygenation of unactivated sp3-C–H bonds. This transformation utilizes Pd(OAc)2 as a catalyst in conjunction with NaNO3 as a redox co-catalyst. Both oxime ether and pyridine derivatives are effective directing groups for these reactions. The oxygen incorporated into the product derives from the solvent (acetic acid). Preliminary results show that the addition of simple NaCl to the reaction mixture results in aerobic chlorination under analogous conditions.

Graphical abstract: Nitrate as a redox co-catalyst for the aerobic Pd-catalyzed oxidation of unactivated sp3-C–H bonds

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Publication details

The article was received on 22 Jun 2012, accepted on 10 Aug 2012 and first published on 30 Aug 2012


Article type: Edge Article
DOI: 10.1039/C2SC20800H
Citation: Chem. Sci., 2012,3, 3192-3195
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    Nitrate as a redox co-catalyst for the aerobic Pd-catalyzed oxidation of unactivated sp3-C–H bonds

    K. J. Stowers, A. Kubota and M. S. Sanford, Chem. Sci., 2012, 3, 3192
    DOI: 10.1039/C2SC20800H

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