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

Wickens, Zachary K. and Morandi, Bill and Grubbs, Robert H. (2013) Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst. Angewandte Chemie International Edition, 52 (43). pp. 11257-11260. ISSN 1433-7851. doi:10.1002/anie.201306756. https://resolver.caltech.edu/CaltechAUTHORS:20131104-143606168

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201306756DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201306756/abstractPublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Issue published online: 14 Oct 2013; Article first published online: 13 Sep 2013; Manuscript Received: 2 Aug 2013. We thank Scott Virgil for technical assistance. We acknowledge KAUST, KFUPM, and NSF for funding and the SNSF for a fellowship to B.M.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)UNSPECIFIED
King Fahd University of Petroleum and Minerals (KFUPM)UNSPECIFIED
NSFUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
Subject Keywords:alkenes; anti-Markovnikov; oxidation; oxygen; palladium
Issue or Number:43
DOI:10.1002/anie.201306756
Record Number:CaltechAUTHORS:20131104-143606168
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20131104-143606168
Official Citation:Wickens, Z. K., Morandi, B. and Grubbs, R. H. (2013), Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst. Angew. Chem. Int. Ed., 52: 11257–11260. doi: 10.1002/anie.201306756
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:42230
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Nov 2013 22:51
Last Modified:10 Nov 2021 16:20

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