Synthesis of Two Types of Nitriles Both Bearing Quaternary Carbon Centers in One-Pot Manner

α-Bromocarboxamides and electrophilic cyanide reagent were transformed into the corresponding α-cyanocarboxamides and ketene imine zinc intermediate in the presence of Zn reductant. Trapping of such Zn species with additional electrophiles resulted another type of nitriles, which realized the synthesis of two types of nitriles both bearing quaternary carbon centers in one-pot manner. This approach could be used to construct C-C, C-S, or C-F bond. Formal synthesis of several key pharmaceutical intermediates including loperamide, proadifen, verapamil, and gallopamil as well as α-fluoroibuprofen and α-fluoroflurbiprofen demonstrated the potential application of this methodology.