Nickel‐Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar‐M (M=MgX, ZnX)
Nickel‐Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar‐M (M=MgX, ZnX)
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DOI：
10.1002/adsc.200404041
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发表时间：
2004-07
影响因子：
5.4
通讯作者：
J. Terao;S. Nii;F. Chowdhury;Akifumi Nakamura;N. Kambe
中科院分区：
文献类型：
--
作者：
J. Terao;S. Nii;F. Chowdhury;Akifumi Nakamura;N. Kambe
开发了一种使用镍催化剂进行卤代烷、1,3-丁二烯和芳基格氏试剂的区域选择性三组分交叉偶联反应的新方法。该反应使用 (dppf)NiCl2 作为催化剂，在 25 °C 下有效进行。烷基氯、烷基溴和烷基碘可以用作合适的烷基化试剂。当使用芳基卤化锌代替格氏试剂时，该反应也会进行。伯烷基溴、仲烷基溴和叔烷基溴的混合物的竞争反应表明，卤化物的反应活性按照伯<仲<叔的顺序增加。提出了一种可能的反应途径，涉及从镍酸盐络合物到卤代烷的单电子转移。
A new method for the regioselective three component cross-coupling reaction of alkyl halides, 1,3-butadienes, and aryl-Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary<secondary<tertiary. A possible reaction pathway involving single electron transfer from a nickelate complex to alkyl halides is proposed.