Nickel-Catalyzed Reductive Benzylation of Aldehydes with Benzyl Halides and Pseudohalides

The reductive benzylation of aromatic and aliphatic aldehydes with benzylic halides is reported using a nickel/zinc catalyst system. In addition to benzylic halides, the first report on the addition of benzylic triflates, acetates, tosylates and tritylates to aldehydes is also presented. By this new method a range of alcohols was synthesized efficiently from aldehydes and benzylic substrates at room temperature in moderate to high yields. The mild reaction conditions and good functional group tolerance make this nickel-catalyzed process synthetically useful for the synthesis of diverse benzylic alcohols.