.png){kind=icon}
.png){kind=icon}
Return
Pyridinium-Derived Mesoionic N-Heterocyclic Olefins (py-mNHOs)
.png){kind=icon}
OA
AI
Q
A
R
P
R
A
M
DOI：10.1002/anie.202318283.png)
.png){kind=icon}
.png){kind=icon}
Share.png){kind=icon}
Save
Abstract
En 中文
Mesoionic polarization allows access to electron-rich olefins that have found application as organocatalysts, ligands, or nucleophiles. Herein, we report the synthesis and characterization of a series of 3-methylpyridinium-derived mesoionic olefins (py-mNHOs). We used a DFT-supported design concept, which showed that the introduction of aryl groups in the 1-, 2-, 4-, and 6-positions of the heterocyclic core allowed the kinetic stabilization of the novel mesoionic compounds. Tolman electronic parameters indicate that py-mNHOs are remarkably strong sigma-donor ligands toward transition metals and main group Lewis acids. Additionally, they are among the strongest nucleophiles on the Mayr reactivity scale. In reactions of py-mNHOs with electron-poor pi-systems, a gradual transition from the formation of zwitterionic adducts via stepwise to concerted 1,3-dipolar cycloadditions was observed experimentally and analyzed by quantum-chemical calculations.
Keywords:
(3+2) Cycloaddition
Mesoions
N-Heterocyclic Olefins
Nucleophilicity
Ylides
AI Summary
Key information extracted from the uploaded paper, including a brief overview, abstract, background, key highlights, visual analysis, and future outlook.
Journal
IF:
16.9
Papers:
5.6W
Citations:
53.0W
Organization
Cited Papers