TY - JOUR T1 - Ni- or Cu-catalyzed cross-coupling reaction of alkyl fluorides with Grignard reagents. AU - Terao,Jun, AU - Ikumi,Aki, AU - Kuniyasu,Hitoshi, AU - Kambe,Nobuaki, PY - 2003/5/8/pubmed PY - 2003/5/8/medline PY - 2003/5/8/entrez SP - 5646 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 19 N2 - n-Octyl fluoride underwent a cross-coupling reaction with n-propylmagnesium bromide in the presence of 1,3-butadiene using NiCl2 as a catalyst at room temperature to give undecane in moderate yields. This alkyl-alkyl cross-coupling proceeded more efficiently when CuCl2 was employed instead of NiCl2. Addition of 1,3-butadiene dramatically improved the yields of the coupling products from primary alkyl Grignard reagents in both Ni- and Cu-catalyzed reactions. Alkyl fluorides efficiently reacted with tertiary alkyl and phenyl Grignard reagents using CuCl2 in the absence of 1,3-butadiene to afford the coupling products in high yields. The competitive reaction of a mixture of alkyl halides (R-X; X = F, Cl, Br) with nC5H11MgBr showed that the reactivities of the halides increase in the order R-Cl < R-F < R-Br. In contrast, in the Cu-catalyzed reaction with PhMgBr, the reactivities increase in the order R-Cl < R-Br < R-F. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12733899/Ni__or_Cu_catalyzed_cross_coupling_reaction_of_alkyl_fluorides_with_Grignard_reagents_ DB - PRIME DP - Unbound Medicine ER -