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A highly regioselective reaction of 2-indolylmethanols with enamides has been developed at room temperature by using AlCl₃ as a catalyst. A wide range of hybrids (40 examples) of indoles and enamides were obtained in moderate to good yields (up to 98% yield). This transformation represents the efficient way to introduce biologically important indoles and enamides skeleton into structurally complex hybrids.