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Angew Chem Int Ed Engl. 2016 Jul 11;55(29):8435-9. doi: 10.1002/anie.201603424. Epub 2016 May 25.

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

Author information

1
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.
2
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA. rhg@caltech.edu.

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.

KEYWORDS:

aldehydes; fluorine; oxidation; palladium; regioselectivity

PMID:
27225538
PMCID:
PMC5013664
DOI:
10.1002/anie.201603424
[Indexed for MEDLINE]
Free PMC Article

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