Year: 2023
Type: article
Abstract: Chiral N -cyclopropyl pyrazoles and structurally related heterocycles are prepared using an earth-abundant copper catalyst under mild reaction conditions with high regio-, diastereo-, and enantiocontrol. The observed N 2:N 1 regioselectivity favors the more hindered nitrogen of the pyrazole. Experimental and DFT studies support a unique mechanism that features a five-centered aminocupration.
DOI: 10.1021/jacs.3c02971
Authors: Minghao Wang, Julie C. Simon, Mengfei Xu, Stephanie A. Corio, Jennifer S. Hirschi, Vy M. Dong
Institutions: University of California, Irvine, Binghamton University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: CAS: Sustainable Technologies for Building Molecules: Cobalt, Nickel, and Copper Catalysis, G1453181110, G1555197637, G1787346651, Track 4: Advanced CI Coordination Ecosystem: Monitoring and Measurement Services, G338811424, G34258105, G3562386289, Track 1: ACCESS Resource Allocations Marketplace and Platform Services (RAMPS), G4010157413, G4275568664, ACO: An Open CI Ecosystem to Advance Scientific Discovery (OpenCI), Track 3: COre National Ecosystem for CyberinfrasTructure (CONECT), G5156331529, G5367127336, G5464919783, G7526614437, G7916508619, Track 2: Customized Multi-tier Assistance, Training, and Computational Help (MATCH) for End User ACCESS to CI, G8499740153, G8994211811, Innovative Tools for Chemical Synthesis: Metal-Hydride Catalysis, Medicinal Motifs, and Molecular Probes, Mechanistic Investigation into Modern Catalytic Reactions
OpenAlex ID: W4382653187