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Origin of Increased Reactivity in Rhenium-Mediated Cycloadditions of Tetrazines

Year: 2021
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Pyridyl tetrazines coordinated to metals like rhenium have been shown to be more reactive in [4 + 2] cycloadditions than their uncomplexed counterparts. Using density functional theory calculations, we found a more favorable interaction energy caused by stronger orbital interactions as the origin of this increased reactivity. Additionally, the high regioselectivity is due to a greater degree of charge stabilization in the transition state, leading to the major product.
DOI: 10.1021/acs.joc.1c01564
Language: English
Field: Chemistry
Open Access status: hybrid
Estimated APC paid: $5,000
Funders: National Science Foundation, Austrian Science Fund, Hochschuljubiläumsstiftung der Stadt Wien, National Institutes of Health, University of California, Los Angeles, National Institute of General Medical Sciences, Division of Chemistry
Awards: G1273626434, Experimental and Theoretical Investigations of Organic Reaction Rates and Mechanisms, Cyclopentadiene Derivatives for Bioorthogonal Cycloadditions, G4898780116, Computational Investigations of Asymmetric Carbon-Carbon Bond Formation, G826464495, G943887615
OpenAlex ID: W3196545702
FWCI: 1.288
Cites: 45
Cited by: 15
Related to: 10