Nickel-Catalyzed Cross-Coupling Reaction of Grignard Reagents with Alkyl Halides and Tosylates: Remarkable Effect of 1,3-Butadienes

作者：Jun Terao, Hideyuki Watanabe, Aki Ikumi, Hitoshi Kuniyasu, Nobuaki Kambe · 发表于：Journal of the American Chemical Society · 年份：2002 · DOI：10.1021/ja025828v · 被引用次数：369 · 研究领域：Catalytic Cross-Coupling Reactions、Coordination Chemistry and Organometallics、Cyclopropane Reaction Mechanisms

A new method for the cross-coupling reaction of Grignard reagents with alkyl chlorides, bromides, and tosylates has been developed by the use of a nickel catalyst in the presence of a diene as an additive. This reaction proceeds efficiently at 0-25 degrees C in THF using primary and secondary alkyl and aryl Grignard reagents. Nickel complexes bearing no phosphine ligands, such as NiCl2, Ni(acac)2, and Ni(COD)2, afford the coupling products in good yields, whereas NiCl2(PPh3)2 and NiCl2(dppp) were less effective. 1,3-Butadiene shows the highest activity as an additive for the present coupling reaction. A plausible reaction pathway was proposed.