Regiocontrolled deprotonative-zincation of bromopyridines using aminozincates

T Imahori, M Uchiyama, T Sakamoto…

Index: Imahori; Uchiyama; Sakamoto; Kondo Chemical Communications, 2001 , # 23 p. 2450 - 2451

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Citation Number: 76

Abstract

In order to investigate regiochemistry in the deprotonative metalation of pyridine, we screened metalating agents and solvents in the lithiation of 2-bromopyridine. To our surprise, when we carried out the reaction of 2-bromopyridine (1) with LTMP and TMSCl using an in situ method at −78 ░C in Et 2 O, the 6-TMS derivative (4) was obtained exclusively in 65% yield (Scheme 2). Related to this unique regioselectivity, Fort and co-workers recently reported a unique ...