Investigations via Kinetics and Multivariate Linear Regression Models of the Mechanism and Origins of Regioselectivity in a Palladium-Catalyzed Aryne Annulation
Year: 2024
Type: article
Abstract: The synthetic potential of unsymmetrically substituted arynes is not yet fully realized due to regioselectivity issues. Although many models exist to predict the regioselectivity of arynes, these models do not hold for metal-mediated reactions. Previously, we reported a way to induce regioselectivity in a metal-catalyzed aryne annulation reaction by using bulky monodentate phosphine ligands. Reported herein is a mechanistic investigation into the operative catalytic cycle within this transformation. Additionally, the molecular parameters responsible for regioselectivity have been examined via LFERs and multivariate linear regression. This model shows the interdependence on both the steric and electronic properties of the aryne and the size of the phosphine ligand for regioselectivity.
Source: ACS Catalysis
Institution: University of Minnesota
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: MRI: Acquisition of a MALDI-TOF/TOF Mass Spectrometer for Molecular Structure Determination and Imaging, G1405578316, G3309432434, G5050677891, Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical Research, G8928599955, Methods for Selective Functionalization of (Hetero)arene Rings
OpenAlex ID: W4403489219