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Angew Chem Int Ed Engl. 2013 Oct 18;52(43):11257-60. doi: 10.1002/anie.201306756. Epub 2013 Sep 13.

Aldehyde-selective Wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst.

Author information

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

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. (18) O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

KEYWORDS:

alkenes; anti-Markovnikov; oxidation; oxygen; palladium

PMID:
24039135
DOI:
10.1002/anie.201306756

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