The first method for directly generating C,N-dianion from an alkyl-substituted π-excessive N-heterocyclic compound (2-methylindole) has been developed. It involves treatment with 3 equiv. of BuLi and 2 equiv. of ButOK in a particular sequence and results in the functionalization of the 2-methyl group of the indole in a regiospecific manner.
S. Inagaki, Y. Nishizawa, T. Sugiura and H. Ishihara, J. Chem. Soc., Perkin Trans. 1, 1990, 179 DOI: 10.1039/P19900000179
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