Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2013 May 22

PMID 23687958

Citations 25

Authors

Satoshi Mizuta

Ida S R Stenhagen

Miriam ODuill

Jamie Wolstenhulme

Anna K Kirjavainen

Sarita J Forsback

Matthew Tredwell

Graham Sandford

Peter R Moore

Mickael Huiban

Sajinder K Luthra

Jan Passchier

Olof Solin

Veronique Gouverneur

Affiliations

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Abstract

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [(18)F]labeling is demonstrated using [(18)F]Selectfluor bis(triflate), a reagent affording [(18)F]tri- and [(18)F]difluoromethylarenes not within reach with [(18)F]F2.

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