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Direct Access to ?-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 ?-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

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

Chu Crystal K CK Ziegler Daniel T DT Carr Brian B Wickens Zachary K ZK Grubbs Robert H RH

Angewandte Chemie (International ed. in English) 20160525 29

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 indu ...[more]

PMID: 27225538

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