Experimental and Theoretical Investigations of Copper‐Catalyzed Chemo‐, Regio‐, and Stereoselective cis ‐Hydroboration of 1,3‐Enynes
Year: 2025
Type: article
Abstract: The mechanistic details of the chemo‐, regio‐, and stereoselective cis ‐hydroboration of 1,3‐enynes were investigated using X‐ray crystallography, kinetic analysis, and density functional theory (DFT) calculations. The kinetic analysis revealed that the reaction is first order in enyne, zeroth order in HBpin, and fractional order in the catalyst. Our studies suggest that a cyclic CuHBpinOAc complex is an off‐cycle species (via DFT analysis) that contributes to the experimentally observed fractional rate order regarding the catalyst. Experimental and computational data suggest that hydrocupration is rate‐limiting and essential for achieving selectivity.
Authors: Farshad Shiri, Nicklas W. Buchbinder, Andrew D. Bage, Reilly Gwinn, Carla Slebodnick, Webster L. Santos, Zhenyang Lin
Institutions: Hong Kong University of Science and Technology, Virginia Tech
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
OpenAlex ID: W4415946887