Facile nucleophilic fluorination reactions using tert-alcohols as a reaction medium: significantly enhanced reactivity of alkali metal fluorides and improved selectivity

…, ST Lim, MH Sohn, JA Katzenellenbogen…

Index: Dong, Wook Kim; Jeong, Hwan-Jeong; Seok, Tae Lim; Sohn, Myung-Hee; Katzenellenbogen, John A.; Dae, Yoon Chi Journal of Organic Chemistry, 2008 , vol. 73, # 3 p. 957 - 962

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Citation Number: 113

Abstract

Although protic solvents are generally not preferred for nucleophilic displacement reactions because of their partial positive charge and hydrogen-bonding capacity that solvate the nucleophile and reduce its reactivity, we recently reported a remarkably beneficial effect of using tertiary alcohols as a reaction media for nucleophilic fluorination with alkali metal fluorides, as well as fluorine-18 radiolabeling with [18F] fluoride ion for the preparation of ...