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

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

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.

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

*Corresponding authors
aKey Laboratory of Green Chemical Media and Reactions, Ministry of Education, College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, China
E-mail: zgs@htu.cn
Tel: +86 373 3325250
Green Chem., 2012,14, 1372-1375

DOI: 10.1039/C2GC00006G

 

http://pubs.rsc.org/en/content/articlelanding/2012/gc/c2gc00006g#!divAbstract

 

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////////Selective reduction, aldehydes and ketones, alcohols,  ammonia borane, neat water

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