Abstract
The reduction of salicylaldehyde by pyridine-borane complex (PB) is much faster than that of other substituted benzaldehydes and ketones (seconds vs hours). Experiments reveal that this acceleration is due to an autocatalytic process involving a pyridinium boronate salt, a component of the equilibrating product mixture from PB reduction of salicylaldehyde. This pyridinium salt behaves as a mild BrOnsted acid and effectively accelerates aldehyde but not ketone reductions by PB. The observation that mild BrOnsted acids are catalysts for PB reductions led to the development of a method using AcOH in CH 2 Cl 2 to promote the selective reduction of aldehydes in the presence of ketones
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