Fluoro??or Trifluoromethyl??Substituted Benzyl and Phenethyl Alcohols: Substrates for Metal??Mediated Site??Selective Functionalization

…, A Spitaleri, F Mongin, M Schlosser

Index: Marzi, Elena; Mongin, Florence; Spitaleri, Andrea; Schlosser, Manfred European Journal of Organic Chemistry, 2001 , # 15 p. 2911 - 2915

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Citation Number: 14

Abstract

Abstract It was possible to functionalize the three fluorobenzyl alcohols and the three 2- (fluorophenyl) ethanols by metalation and subsequent carboxylation, the prototype electrophilic trapping reaction. Triisopropylsilyl (TIPS) outperformed methoxymethyl (MOM) as an O-protective group making seven new fluorobenzoic acids accessible in 63% average yield. Moreover, the TIPS group tolerates weakly basic and acidic media and, therefore, ...