biostudies-literatureUnknown12(32)Cheng YIt is very important to develop multiple C-H substitution reactions of simple alkenes to obtain complex unsaturated components. The present study focuses on a theoretical investigation of the plausible mechanism in the Fe(OTf)₃-catalyzed tandem amidomethylative reactions of α-phenylstyrene. Bis(tosylamido)methane is activated by Fe(OTf)₃ to form tosylformaldimine and its Fe(OTf)₃-adduct. The Fe(OTf)₃-adduct undergoes an intermolecular aza-Prins reaction with α-phenylstyrene to form allylamide. The DFT data support the formation of the hexahydropyrimidine derivative from allylamide, and "condensation/iminium homologation/intramolecular aza-Prins" is the optimal reaction path. At the same time, a possible reaction pathway for the conversion of the RSC advances20523-20529https://www.ebi.ac.uk/biostudies/studies/S-EPMC9284522biostudies-literatureMechanism of the Fe(iii)-catalyzed synthesis of hexahydropyrimidine with α-phenylstyrene: a DFT study.PMC9284522Liu HZhao CYang SCheng YfalseMechanism of the Fe(iii)-catalyzed synthesis of hexahydropyrimidine with α-phenylstyrene: a DFT study.It is very important to develop multiple C-H substitution reactions of simple alkenes to obtain complex unsaturated components. The present study focuses on a theoretical investigation of the plausible mechanism in the Fe(OTf)₃-catalyzed tandem amidomethylative reactions of α-phenylstyrene. Bis(tosylamido)methane is activated by Fe(OTf)₃ to form tosylformaldimine and its Fe(OTf)₃-adduct. The Fe(OTf)₃-adduct undergoes an intermolecular aza-Prins reaction with α-phenylstyrene to form allylamide. The DFT data support the formation of the hexahydropyrimidine derivative from allylamide, and "condensation/iminium homologation/intramolecular aza-Prins" is the optimal reaction path. At the same time, a possible reaction pathway for the conversion of the 2022-01-01T00:00:00Z2022 Jul2025-04-21T22:29:29.256Z2025-04-05T18:48:38.937ZS-EPMC92845223591916910.1039/d2ra02727e