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

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Morandi,  Bill
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA);
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wickens, Z. K., Morandi, B., & Grubbs, R. H. (2013). Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst. Angewandte Chemie International Edition, 52(43), 11257-11260. doi:10.1002/anie.201306756.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-BA8F-E
Abstract
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