Addition of Hydride Reduction to Alcohols or Amines

Simple hydrides such as sodium or potassium hydride are too insoluble in organic solvents to be useful in reductions. The compounds sodium borohydride, Na[BHj, and lithium aluminum hydride, Li[AlHj, are the usual sources of hydride for carbonyl reduction reactions. 

FIGURE 14.47 Desulfurization of a thioacetal using Raney nickel 

FIGURE 14.49 Reduction of acetophenone with lithium aluminum hydride gives a racemic product. 

FIGURE 14.50 Diastereomeric reduction products are produced in unequal amounts. 

FIGURE 14.52 imine reduction using sodium borohydride. 

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