Hydrogen-mediated carbon-carbon bond formations: applied to reductive aldol and Mannich reactions



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Hydrogen gas is the cleanest and most cost-effective reductant available to mankind, and the use of hydrogen gas in catalytic hydrogenation reactions is one of the oldest and most utilized organic reactions. Although catalytic hydrogenation has been practiced in industry on enormous scale, the use of hydrogen gas as a terminal reductant in C-C bond forming reactions has been limited to processes involving the migratory insertion of carbon monoxide such as: alkene hydroformylation and the Fischer-Tropsch reaction. A significant advance to the field of synthetic organic chemistry would be the expansion of C-C bond forming reactions beyond reductive coupling via carbon monoxide insertion. Herein, related metal catalyzed reductive couplings to [alpha],[beta]-unsaturated compounds in the presence of reducing agents such as: silane, borane, and hydrogen are reviewed. The following chapters discuss the development of hydrogen-mediated reductive aldol and Mannich reactions. The results from this body of work clearly demonstrate that hydrogen-mediated C-C bond forming reactions are emerging as a powerful tool for synthetic chemists.