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

Preview

PDF - Supplemental Material
See Usage Policy.
765kB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20131104-143606168

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:

URL	URL Type	Description
http://dx.doi.org/10.1002/anie.201306756	DOI	Article
http://onlinelibrary.wiley.com/doi/10.1002/anie.201306756/abstract	Publisher	Article

ORCID:

Author	ORCID
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 Agency	Grant Number
King Abdullah University of Science and Technology (KAUST)	UNSPECIFIED
King Fahd University of Petroleum and Minerals (KFUPM)	UNSPECIFIED
NSF	UNSPECIFIED
Swiss National Science Foundation (SNSF)	UNSPECIFIED

Subject Keywords:

alkenes; anti-Markovnikov; oxidation; oxygen; palladium

Issue or Number:

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

Repository Staff Only: item control page