Synlett 2005(1): 182-183  
DOI: 10.1055/s-2004-837192
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Sodium Borohydride - A Versatile Reducing Agent

Li Zhenjiang*
College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, 210009, P. R. China
e-Mail: zj.lee@163.com;
Further Information

Publication History

Publication Date:
07 December 2004 (online)

Introduction

The use of alkali metal borohydrides as reducing agents in organic chemistry is well documented since the pioneering work by H. C. Brown and colleagues. [1] After its first application in carbonyl reduction, [2] sodium borohydride has been widely used as an economical and mild reducing agent in the reduction of carbonyl and related compounds as well as other unsaturated compounds. [3] Suitable substrates [4] included conjugated carbonyl compounds, alkoxysulfonium salts, nitro compounds, carboxylic acids and esters, sulfonate esters, alkyl halides, nitriles, and amides. It was observed that the reducing activity was influenced by solvents and metal ions, [5] and can be finely adjusted by Lewis acid mediation. [6] Reduction in acidic media [7] was investigated extensively. Sodium borohydride (NaBH4) is commercially available as a white crystalline powder with moderate hygroscopic property. It can be used as solution in lower alcohols, or in glymes for elevated temperature. In neutral and acidic water, NaBH4 hydrolyzes to afford hydrogen gas, but a basic aqueous solution of NaBH4 is stable and useful in the lab.

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