DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane.

ABSTRACT: Metal-free boron Lewis acids, tris(pentafluorophenyl)borane B(C₆F₅)₃, have the advantages of low toxicity and low cost and are a promising catalyst. A density functional theory (DFT) calculation was used to clarify the mechanism and the origin of the diastereoselective cyclopropanation of aryldiazodiacetate and styrene derivatives catalyzed by B(C₆F₅)₃. Four pathways were calculated: B(C₆F₅)₃-catalyzed N-, C-, and O-bound boron-activated aryldiazodiacetate and without B(C₆F₅)₃ catalysis. By calculating and comparing the energy barriers, the most possible reaction mechanism was proposed, that is, first, B(C₆F₅)₃ catalyzed O-boun

SUBMITTER: Wen X 

PROVIDER: S-EPMC9025995 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature