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.

SUBMITTER: Chu CK 

PROVIDER: S-EPMC5013664 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature