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Published July 11, 2016 | Accepted Version + Supplemental Material
Journal Article Open

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


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.

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.

Attached Files

Accepted Version - nihms791533.pdf

Supplemental Material - anie201603424-sup-0001-misc_information.pdf


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