Ni-catalyzed alkylative dimerization of vinyl Grignard reagents using alkyl fluorides

J Terao, H Watabe, N Kambe

Index: Terao, Jun; Watabe, Hiroyasu; Kambe, Nobuaki Journal of the American Chemical Society, 2005 , vol. 127, # 11 p. 3656 - 3657

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Citation Number: 61

Abstract

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, PhCH CHMgBr gave double alkylative vinyl coupling product 4 in good yield as the sole coupling product. Alkyl fluorides react as the most suitable alkylating ...