Controllable Regioselective [3+2] Cyclizations of <i>N</i>-CF<sub>3</sub> Imidoyl Chlorides and Ph<sub>3</sub>PNNC: Divergent Synthesis of <i>N</i>-CF<sub>3</sub> Triazoles
Yan Fang Gao, Ru Zhong Zhang, Cong Xu, Mang Wang
Abstract
Presented herein are two distinct regiodivergent [3+2] cyclization reactions between N -CF 3 imidoyl chlorides and N -isocyaniminotriphenylphosphorane (NIITP) that include flexible modulation of the electronic properties of NIITP. The regioselectivity of reactions was different in the absence and presence of the Mo catalyst. The approach provides alternative efficient and scalable routes for N -CF 3 triazole synthesis, demonstrating a broad substrate scope, excellent functional group tolerance, and practical advantages.
Topics & Concepts
RegioselectivityChemistryStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods