Ni-catalyzed alkylative dimerization of vinyl Grignard reagents using alkyl fluorides
Ni-catalyzed alkylative dimerization of vinyl Grignard reagents using alkyl fluorides
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DOI：
10.1021/ja042565r
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发表时间：
2005-03-23
影响因子：
15
通讯作者：
Kambe, N
中科院分区：
文献类型：
--
作者：
Terao, J;Watabe, H;Kambe, N
在镍催化剂存在下，卤代烷与乙烯基氯化镁发生独特的交叉偶联反应，高产率地合成了2-烷基-3-丁烯基格氏试剂（1）。该反应在25 °C下在THF中使用伯烷基氟化物和仲烷基氟化物有效地进行。而PhCHCHMgBr作为唯一的偶联产物，以较好的产率得到双烷基化乙烯基偶联产物4。与相应的氯化物、溴化物和碘化物相比，烷基氟化物作为最合适的烷基化试剂反应。
Alkyl halides underwent unique cross-coupling reaction with vinylmagnesium chloride in the presence of Ni catalyst to give 2-alkyl-3-butenyl Grignard reagent (1) in high yields. This reaction proceeded efficiently at 25 °C in THF using primary and secondary alkyl fluorides. On the other hand, PhCHCHMgBr gave double alkylative vinyl coupling product4in good yield as the sole coupling product. Alkyl fluorides react as the most suitable alkylating reagent in comparison to the corresponding chlorides, bromides, and iodides.