Reaction of Potassium Triphenylborohydride with Selected Organic Compounds Containing Representative Functional Groups

Article abstract of DOI:10.1021/jo00234a011

Potassium triphenylborohydride (KTPBH) is a very mild reducing agent.With the exception of aldehyde, ketone, quinone, phenyl isocyanate, n-alkyl iodide, and aromatic disulfide, most functional groups studied react slowly or are inert toward KTPBH.KTPBH exhibits a remarkable stereoselectivity in the reduction of cyclic ketones.The reductions of epoxides are very slow, but the presence of the Lewis acid Ph3B dramatically accelerates the rates and chenges the regioselectivity in the case of trisubstituted epoxides.