Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

The use of alkylorganometallic reagents in metal-catalyzed cross-coupling towards the development of catalytic procedures using a wide range of coupling partners, metal catalysts, and diverse organometallics, is reviewed. Fu and co-workers reported Ni-catalyzed C(sp3)-C(sp3) cross-coupling reactions of diverse alkylzinc reagents with unactivated secondary alkyl halides under very mild conditions. Differences in rate when varying the structure of boron reagents is found, the B-alkyl-9-BBN derivative was found to be significantly more reactive toward bromobenzene than the corresponding B-alkyl-OBBD counterpart. Narukawa and co-workers reported an efficient synthesis of 2-alkyl carbapenems via Pd-catalyzed alkylation of carbapenem-2-yl triflate with B-alkyl-9-BBN. In 2009, the synthesis of unsymmetrical 3,4-disubstituted maleimides by a sequential one-pot Pdcatalyzed cross-coupling reaction of indiumorganometallics with 3,4-dihalomaleimides, was reported.