Chemoselective reductions with sodium borohydride
Abstract
Under the appropriate reaction conditions, sodium borohydride is a highly chemoselective reducing agent. The order of reactivity among carbonyl groups is conjugated enones < ketones < conjugated aldehydes < aldehydes. In general, a carbonyl group of one type can be selectively reduced in the presence of a carbonyl group of a less reactive type. Reactions are conducted with excess sodium borohydride at −78 °C in solvent mixtures of methanol or ethanol in dichloromethane. Keywords: sodium borohydride, chemoselective reductions.
Résumé
Utilisé dans des conditions réactionnelles appropriées, le borohydrure de sodium est un agent de réduction très chémosélectif. Pour les groupements carbonyles, l'ordre de réactivité est le suivant: énones conjuguées < cétones < aldéhydes conjugués < aldéhydes. En général, un certain type de groupement carbonyle peut être réduit sélectivement lorsqu'il est en présence d'un autre groupement carbonyle d'un type moins réactif. On réalise ces réactions en opérant en présence d'un excès de borohydrure de sodium, à −78 °C, dans des mélanges de solvants formés de méthanol ou d'éthanol avec du dichlorométhane. Mots clés : borohydrure de sodium, réductions chémosélectives. [Traduit par la revue]
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Published In
Canadian Journal of Chemistry
Volume 67 • Number 7 • July 1989
Pages: 1206 - 1211
History
Version of record online: 5 February 2011
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Dale E. Ward and Chung K. Rhee. 1989. Chemoselective reductions with sodium borohydride. Canadian Journal of Chemistry.
67(7): 1206-1211. https://doi.org/10.1139/v89-182
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