The Journal of organic chemistry

Substitution of Hydroxybiaryls via Directed o rtho-Lithiation of N-Silylated O-Aryl N-Isopropylcarbamates

M Kauch, V Snieckus, D Hoppe

Index: Kauch, Matthias; Snieckus, Victor; Hoppe, Dieter Journal of Organic Chemistry, 2005 , vol. 70, # 18 p. 7149 - 7158

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Citation Number: 28

Abstract

Herein we report regioselective substitution reactions of a series of 2-and 3-hydroxybiaryls including BINOL via a new directed ortho-metalation procedure. O-Aryl N- isopropylcarbamates, conveniently prepared from phenols and isopropyl isocyanate, are temporarily and in situ N-protected by means of silyl triflates to form stable intermediates for low temperature lithiation reactions using butyllithium/TMEDA in diethyl ether. The ...