Mechanism of the Fe(iii)-catalyzed synthesis of hexahydropyrimidine with α-phenylstyrene: a DFT study.

ABSTRACT: 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

SUBMITTER: Cheng Y 

PROVIDER: S-EPMC9284522 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature