A new pathway for benzylation of nitriles is being developed based on palladium-catalyzed deacylative benzylation. In this process, the benzylic alcohol and a-nitrile ester pronucleophile coupling partners undergo in situ retro-Claisen activation to generate a benzylic carbonate and a carbanion. These reactive intermediates are then coupled back together to form a-benzylated nitriles in the presence of palladium. This new method works under mild conditions with the direct use of inexpensive, readily available benzylic alcohols and avoid the use of toxic benzylic halides.

Palladium-catalyzed deacylative benzylation of nitriles

245th National Meeting (2013)

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