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Bromine–magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex n Bu 2 i PrMgLi: a new preparation methodology of functionalized picolines …

S Kii, A Akao, T Iida, T Mase, N Yasuda

Index: Kii, Satoshi; Akao, Atsushi; Iida, Takehiko; Mase, Toshiaki; Yasuda, Nobuyoshi Tetrahedron Letters, 2006 , vol. 47, # 12 p. 1877 - 1879

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Citation Number: 13

Abstract

The organomagnesium complex nBu2iPrMgLi, readily prepared from nBuLi and iPrMgCl (2: 1), is quite efficient for the bromine–magnesium exchange of 5-bromo-2-picoline under noncryogenic conditions (at− 10° C). The resulting picolylmagnesium complex reacts with various electrophiles to afford functionalized picolines.