N-(α-Aminoalkyl)benzotriazoles: Novel 'Nonstabilized' α-Aminocarbanion Synthons

C−Benzotriazole bonds were selectively transformed to give the corresponding α-aminocarbanions when N-(α-aminoalkyl)benzotriazoles were reacted with either Li/LiBr or SmI2 in the presence of representative electrophiles. The ranges of applicability of the two reagents complement each other, and together the two protocols provide a general route from readily available crystalline starting materials to a variety of “nonstabilized” α-aminocarbanions that can be trapped in moderate to good yields.