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SELECTIVE ALDEHYDE REDUCTION IN KETOALDEHYDES WITH NaBH4-Na2CO3-H2O AT ROOM TEMPERATURES

Chandrasekhar, Sosale and Shrinidhi, Annadka (2014) SELECTIVE ALDEHYDE REDUCTION IN KETOALDEHYDES WITH NaBH4-Na2CO3-H2O AT ROOM TEMPERATURES. In: SYNTHETIC COMMUNICATIONS, 44 (14). pp. 2051-2056.

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Official URL: http://dx.doi.org/10.1080/00397911.2014.888751

Abstract

A variety of aliphatic and aromatic ketoaldehydes were reduced to the corresponding ketoalcohols with a mixture of sodium borohydride (1.2 equivalents) and sodium carbonate (sixfold molar excess) in water. Reactions were performed at room temperatures over (typically) 2 h, and yields of isolated products generally ranged from 70% to 85%. A biscarbonate-borane complex, (BH3)(2)CO2](2-) 2Na(+), possibly formed from the reagent mixture, is likely the active reductant. The moderated reactivity of this acylborane species would explain the chemoselectivity observed in the reactions. The readily available reagents and the mild aqueous conditions make for ease of operation and environmental compatibility, and make a useful addition to available methodology.

Item Type: Journal Article
Additional Information: copyright for this article belongs to TAYLOR & FRANCIS INC, 530 CHESTNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA
Keywords: Acylborane; aldehyde; aqueous; borane; borohydride; chemoselective; reduction
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 19 Aug 2014 09:24
Last Modified: 19 Aug 2014 09:24
URI: http://eprints.iisc.ac.in/id/eprint/49576

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