Transition metal-catalyzed hydrogenation of carbon-carbon multiple bond is one of the most important reactions in synthetic and industrial chemistry. Hydrogen gas is usually used in the hydrogenation reaction, however, it requires handling of highly flammable hydrogen gas and pressurized conditions. Although metal hydrides, such as LiAIH_4 and Bu~i_2AlH, can be used as the reducing agent, cost and functional group-compatibility of the metal hydride reagents often become a problem. Catalytic transfer hydrogenation using simple alcohols, such as MeOH and Pr~iOH, and transition metal catalysts is an attractive method since it dose not require the pressurized conditions and expensive reagents. Recently, a research group of Shirakawa and Hayashi has reported the hydrogenation of alkynes to alkenes using D_2O or H_2O as hydrogen source and hexamethyldisilane as reducing agent in the presence of palladium catalyst. Here we report a rhodium-catalyzed hydrogenation of olefins including alpha,beta-unsaturated ketones using H_2O or D_2O as hydrogen source and zinc metal as reducing agent.
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