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

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.