Borohydride refers to the anion BH4− and its salts. Borohydride is also the term used for compounds containing BH4-nXn-, for example cyanoborohydride (B(CN)H3-) and triethylborohydride (B(C2H5)3H-). Such compounds find wide use as reducing agents in organic synthesis.
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- The nucleophilic borohydrides-sodium borohydride [NaBH4], lithium borohydride [LiBH4], zinc borohydride [Zn(BH4)2], lithium- and potassium trialkylborohydrides [Li-, K-R3BH], and sodium cyanoborohydride [NaBH3CN]-exhibit, depending on the metal cation and the ligands, characteristic reducing properties toward functional groups. All borohydrides reduce aldehydes and ketones; reduction of esters and carboxylic acids to primary alcohols requires specific reagents.
- George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 4 : Functional Group Transformations: Oxidation and Reduction