A simple and efficient methodology for the first synthesis of tri- and di-fluoromethyl-bis(indolyl)methanols has been demonstrated through a one-pot Friedel-Crafts-type acylation-alkylation of readily available indoles and fluorinated acids. This simple protocol was successfully performed under metal-, additive-, toxic-solvent-, and protective-gas-free conditions, and delivered a wide range of tri- and di-fluoromethyl-bis(indolyl)methanols in moderate to high yields. Notably, this reaction can tolerate diverse vital and reactive functional groups. Furthermore, this one-pot Friedel-Crafts-type acylation-alkylation can be readily expanded to the gram scale with no obvious decrease in the yield, demonstrating its high application potential.