Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst
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AbstractBreaking 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.
CitationWickens ZK, Morandi B, Grubbs RH (2013) Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst. Angew Chem 125: 11467–11470. Available: http://dx.doi.org/10.1002/ange.201306756.
SponsorsWe thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M.