Contribution of heterobifunctional ligands to transition metal-catalysed C–C coupling reactions

In this account the authors’ latest results in C–C coupling catalysis are reviewed. First, an efficient catalytic system for the Kumada–Tamao–Corriu coupling reaction based on NHC-phosphine (NHC = N-heterocyclic carbene) nickel complexes is presented. Then the use of palladium complexes of chiral ferrocenyl NHC-phosphines in the asymmetric Suzuki–Miyaura coupling reaction is reported. High catalytic activities and moderate enantioselectivities (ee up to 46%) were obtained. Chiral ferrocenyl phosphine–ethers were also tested in the asymmetric Suzuki–Miyaura reaction yielding good activities and moderate enantioselectivities (ee up to 37%). Finally, the original synthesis of a ferrocenyl rhodium(III) complex and its successful use as catalyst for a C–C coupling reaction via C–H activation of 2-phenylpyridine is presented.