"Sandwich" Diimine-Copper Catalyzed Trifluoroethylation and Pentafluoropropylation of Unactivated C(sp³ )-H Bonds by Carbene Insertion.

ABSTRACT: We report here "sandwich"-diimine copper complex-catalyzed trifluoroethylation and pentafluoropropylation of unactivated C(sp³ )-H bonds in alkyl esters, halides, and protected amines by employing CF₃ CHN₂ and CF₃ CF₂ CHN₂ reagents. Reactions proceed in dichloromethane solvent at room temperature. Identical C-H functionalization conditions and stoichiometries are employed for generality and convenience. Selectivities for C-H insertions are higher for compounds possessing stronger electron-withdrawing substituents. Preliminary mechanistic studies point to a mechanism involving a pre-equilibrium forming a "sandwich"-diimine copper-CF₃ CHN₂ complex followed by rate-determining loss of nitrogen affording th

SUBMITTER: Le TV 

PROVIDER: S-EPMC10642771 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature