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An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected anilines with deactivated CF3-indole-3-carbinols promoted by In(OTf)3 has been developed. A series of diversified trifluoromethylated (indolyl)phenylmethanes were produced featuring the C-alkylation in moderate to high chemical yields and with high regioselectivities.