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Issue 5, 2012
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Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

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Abstract

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.

Graphical abstract: Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

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Publication details

The article was received on 04 Jan 2012, accepted on 20 Feb 2012 and first published on 16 Mar 2012


Article type: Paper
DOI: 10.1039/C2GC00006G
Green Chem., 2012,14, 1372-1375

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    Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

    L. Shi, Y. Liu, Q. Liu, B. Wei and G. Zhang, Green Chem., 2012, 14, 1372
    DOI: 10.1039/C2GC00006G

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