Catalytic Hydration of Terminal Alkenes to Primary Alcohols

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Abstract
Direct catalytic hydration of terminal alkenes to primary alcohols would be an inexpensive route to industrially useful alcohols and a convenient synthetic route for the synthesis of terminal alcohols in general. The reaction betweentrans-PtHCl(PMe3)2(where Me = CH3) and sodium hydroxide in a one-to-one mixture of water and 1-hexene yields a species that, at 60°C and in the presence of the phasetransfer catalyst benzyltriethylammonium chloride, catalyzes selective hydration of 1-hexene ton-hexanol at a rate of 6.9 ± 0.2 turnovers per hour. Hydration of 1-dodecene ton-dodecanol occurs at a rate of 8.3 ± 0.4 turnovers per hour at 100°C. Deuterium labeling experiments withtrans-PtDCl(PMe3)2show that hydration involves reductive elimination of a C—H bond. At low hydroxide concentrations (k1= 9.3 ± 0.5 × 10-3liters per mol per second) appears to be limiting under these conditions.