Sodium borohydride in carboxylic acid media: a phenomenal reduction system
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 27 (6) , 395-404
- https://doi.org/10.1039/a827395z
Abstract
The union of sodium borohydride and carboxylic acids has yielded an amazingly versatile and efficient set of reducing reagents. These acyloxyborohydride species reduce and N-alkylate indoles, quinolines, isoquinolines, related heterocycles, imines, enamines, oximes, enamides, and similar functional groups. They reduce amides and nitriles, aryl alcohols and ketones, aldehydes in the presence of ketones, and β-hydroxyketones to 1,3-diols stereoselectively. This reagent is also extraordinarily useful for the N-alkylation of primary and secondary amines with aldehydes and ketones in a novel reductive amination process.Keywords
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