α-Difluoromethylation on sp3 Carbon of Nitriles Using Fluoroform and Ruppert–Prakash Reagent

Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the α-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the α-siladifluoromethylated nitrile products, which can be utilized for sequential carbon-carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.