Nickel Catalyzed Alkylation of 2-Chloro-Pyridine. A Facile Synthesis of ω-(2-Pyridyl)-Alkylic Alcohols

Abstract

The nickel complex catalyzed cross-coupling reaction of Grignard reagents with sp²−carbon halides is a very efficient method for selective carbon-carbon bond formation and it has found wide-spread use in organic synthesis.¹ However, the extension of this reaction to substrates having hydroxyl groups has not been reported.² As a part of synthetic project, we needed a convenient and experimentally simple method for preparing ω-(2-pyridyl)-alkylic alcohols (I), possible precursors of conjugated diene pheromones,^3–5 and decided to choose the nickel catalyzed route to obtain these compounds starting from 2-chloro-pyridine (Scheme).