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Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst

Authors

  • Zachary K. Wickens,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • Dr. Bill Morandi,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • Prof. Dr. Robert H. Grubbs

    Corresponding author
    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
    • Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)

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  • We thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M.

Abstract

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Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

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