Catalytic Formation of Carbon–Carbon Bonds by Activation of Carbon–Hydrogen Bonds

Abstract

The direct functionalization of C–H bonds by formation of a C–C bond is an interesting and important alternative to coupling reactions involving halide derivatives. These reactions are complex but during the past few years a number of new systems have been developed which display promising scope. This microreview will briefly mention the different mechanisms leading to C–H activation and describe the new systems leading to the catalytic formation of carbon–carbon bonds.

Synthesis and reactivity towards carbon monoxide of an optically active endo five-membered ortho-cyclopalladated imine: X-ray molecular structure of trans-(μ-Cl)2[Pd(κ2-C,N-(R)-C6H4-CH N-CHMe-Ph)]2

“…Thus, from samples A and B, it was possible to assign the characteristic NMR proton resonances and IR absorptions for compounds 11 and 12 (see Section 3). Furthermore, the FAB(+) mass spectrum of sample A produced the most abundant peaks at 268 and 236, which corresponded to the molecular monopositive cations [M 11 +H + ] and [M 11 +H + -MeOH], and the CI mass spectrum of sample B displayed the most abundant peak at 268, which corresponded to the molecular monopositive cation [M 12 +H + ], where M 11 and M 12 were the masses of the most abundant isotopomer of 11 and 12, respectively.…”

Addition of Arenes to Ethylene and Propene Catalyzed by Ruthenium

“…1,2 Although many transition metal complexes that initiate C-H oxidative addition have been reported, [3][4][5] efficient chemical synthesis via catalytic C-H bond activation and subsequent C-C bond formation remains a challenging goal. [6][7][8] Significant recent advancements in the arena of catalytic C-H activation have been reported for aromatic systems; 9 however, such reactions are primarily limited to aromatic systems with heteroatomic functionality. For example, rutheniumor rhodium-catalyzed C-H activations of aromatic ketones and subsequent C-C bond formation with alkenes or alkynes have been reported.…”

Theoretical investigation of Ni(PMe3)4-catalyzed intermolecular hydroacylation of alkynes with benzaldehydes

“…Transition metal-catalyzed C-H bond activation has received considerable attention in synthetic organic chemistry, as the cleavage of an unreactive C-H bond and the subsequent addition of the C-H unit to unsaturated substrates such as alkenes and alkynes can lead to the formation of a new C-C bond [1][2][3][4][5][6][7]. During the last two decades, many successful applications of catalytic C-H bond activation to give new C-C bonds have been reported [8].…”