METHOD FOR THE BENZOTRIAZOLE-MEDIATED SYNTHESIS OF ALPHA-SILYLALKYLATED HETEROCYCLES AND N,N-DIALKYLANILINES

N-(Benzotriazol-1-ylmethyl)carbazole and -indole undergo lithiation with butyllithium. The resulting anions react with a variety of silyl chlorides to give silylated intermediates which are transformed by displacement of the benzotriazolyl group with Grignard reagents into the corresponding alpha-silylalkylated heterocycles in excellent overall yields. Applying the same method to N,N-dimethylaniline leads to a novel approach for the synthesis of its 4-alpha-silylalkylated analogs.