Benzotriazole-Triggered Three-Component Lewis Acid-Catalyzed Ring-Opening 1,3-Aminofunctionalization of Donor–Acceptor Cyclopropanes
Shiksha Deswal, Avishek Guin, Akkattu T. Biju
Abstract
The use of benzotriazoles as nucleophilic triggers in the three-component Yb(OTf) 3 -catalyzed ring-opening 1,3-aminofunctionalization of donor–acceptor (D–A) cyclopropanes is presented. Using N -halo succinimide (NXS) as the third component, the reaction afforded the 1,3-aminohalogenation product in up to an 84% yield. Moreover, using alkyl halides or Michael acceptors as the third components, the 3,1-carboaminated products are formed in up to a 96% yield in a one-pot operation. Employing Selectfluor as the electrophile, the reaction furnished the 1,3-aminofluorinated product in a 61% yield.
Topics & Concepts
ChemistryBenzotriazoleRing (chemistry)Component (thermodynamics)CatalysisLewis acids and basesAcceptorStereochemistryFrustrated Lewis pairMedicinal chemistryCombinatorial chemistryOrganic chemistryThermodynamicsCondensed matter physicsPhysicsCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods