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Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation

Chu, Crystal K. and Ziegler, Daniel T. and Carr, Brian and Wickens, Zachary K. and Grubbs, Robert H. (2016) Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation. Angewandte Chemie International Edition, 55 (29). pp. 8435-8439. ISSN 1433-7851. PMCID PMC5013664. http://resolver.caltech.edu/CaltechAUTHORS:20160601-104322126

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Abstract

An aldehyde-selective Wacker-type oxidation of allylic fluorides proceeds with a nitrite catalyst. The method represents a direct route to prepare β-fluorinated aldehydes. Allylic fluorides bearing a variety of functional groups are transformed in high yield and very high regioselectivity. Additionally, the unpurified aldehyde products serve as versatile intermediates, thus enabling access to a diverse array of fluorinated building blocks. Preliminary mechanistic investigations suggest that inductive effects have a strong influence on the rate and regioselectivity of the oxidation.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201603424DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201603424/abstractPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5013664PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: April 7, 2016; Revised: April 26, 2016; First published: 25 May 2016. We thank Dr. David VanderVelde for NMR assistance and Dr. Peter Dornan for helpful discussions. We acknowledge KFUPM and ONR for financial support and the NIH NIGMS (F32GM116357) for a fellowship to D.Z.
Funders:
Funding AgencyGrant Number
King Fahd University of Petroleum and Minerals (KFUPM)UNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
NIH Postdoctoral FellowshipF32GM116357
Subject Keywords:aldehydes; fluorine; oxidation; palladium; regioselectivity
PubMed Central ID:PMC5013664
Record Number:CaltechAUTHORS:20160601-104322126
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160601-104322126
Official Citation:C. K. Chu, D. T. Ziegler, B. Carr, Z. K. Wickens, R. H. Grubbs, Angew. Chem. Int. Ed. 2016, 55, 8435.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67537
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:01 Jun 2016 19:46
Last Modified:17 Jul 2017 21:55

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