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Ammonia borane as a metal free reductant for ketones and aldehydes: a mechanistic study


Yang, X; Fox, T; Berke, H (2011). Ammonia borane as a metal free reductant for ketones and aldehydes: a mechanistic study. Tetrahedron, 67(37):7121-7127.

Abstract

Without a catalyst ketones and aldehydes were reacted in THF with ammonia borane (AB) to proceed hydroboration forming alkyl borates. Mechanistic studies revealed that dissociation of ammonia from AB occurred before the hydroboration step. When methanol was used as the solvent, metal free methanolysis of AB would take place with the ketone/aldehyde being directly hydrogenated by the MeOH center dot BH(3) complex. (C) 2011 Elsevier Ltd. All rights reserved.

Without a catalyst ketones and aldehydes were reacted in THF with ammonia borane (AB) to proceed hydroboration forming alkyl borates. Mechanistic studies revealed that dissociation of ammonia from AB occurred before the hydroboration step. When methanol was used as the solvent, metal free methanolysis of AB would take place with the ketone/aldehyde being directly hydrogenated by the MeOH center dot BH(3) complex. (C) 2011 Elsevier Ltd. All rights reserved.

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17 citations in Web of Science®
22 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:September 2011
Deposited On:05 Mar 2012 15:57
Last Modified:05 Apr 2016 15:41
Publisher:Elsevier
ISSN:0040-4020
Publisher DOI:https://doi.org/10.1016/j.tet.2011.06.104
Other Identification Number:ISI:000294574400016

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