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




Mizuta S, Stenhagen ISR, O'Duill M, Wolstenhulme J, Kirjavainen AK, Forsback SJ, Tredwell M, Sandford G, Moore PR, Huiban M, Luthra SK, Passchier J, Solin O, Gouverneur V

PublisherAMER CHEMICAL SOC

2013

Organic Letters

ORGANIC LETTERS

ORG LETT

11

15

11

2648

2651

4

1523-7060

DOIhttps://doi.org/10.1021/ol4009377



Treatment of readily available alpha,alpha-difluoro- and alpha-fluoroarylacetic acids with Selecffluor 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 [F-18]labeling is demonstrated using [F-18]Selectfluor bis(triflate), a reagent affording [F-18]tri- and [F-18]difluoromethylarenes not within reach with [F-18]F-2.



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