The hydroboration of carbonyls serves as a facile, atom-efficient means of reducing ketones and aldehydes. Hydrolysis of the resulting boryl ester yields the corresponding alcohol, or the borane can be exchanged through Suzuki cross-coupling to yield a functionalized ether. The fast and clean hydroboration of ketones and aldehydes is reported using 0.1 mol% La[N(TMS)2, an inexpensive, commercially available catalyst. It is proposed that the lanthanum activates the carbonyl as a Lewis acid and pinacolborane then reacts. Despite ketones reacting more quickly, a preference for aldehydes is seen. A mechanistic study is currently underway.

Lanthanide-catalyzed hydroboration of carbonyls

252nd National Meeting (2016)

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