Year: 2025
Type: article
Abstract: An isolable ring-fused pyridinylidene (a so-called Hammick intermediate) was synthesized from a benzo[ h ]isoquinolinium salt, and its structure in the solid state was determined. The isolation of this first-of-its-kind pyridine-derived aromatic N-heterocyclic carbene was made possible due to the presence of an adamantyl group on nitrogen, forcing the nitrogen to be planar and enhancing both π-donation and steric protection, and to its unique polycyclic structure, which displays an intramolecular C–H···C carbene interaction. Additionally, an example of isomerization of a carbene into another carbene, namely, a benzo[ h ]isoquinolin-1-ylidene into a benzo[ h ]isoquinolin-3-ylidene, is reported.
DOI: 10.1021/jacs.5c05642
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Chiral Cyclic Alkyl Amino Carbenes in Asymmetric Catalysis, G1955154579, G3010527862, Straightforward access to enantiopure NHC-Transition Metal Complexes: New opportunities for asymmetric catalysis, Highly Electron-Deficient Carbon, Boron and Silicon Compounds, Helicenic N-heterocyclic carbenes (helicenic NHCs): synthesis, structure, photophysical properties and catalytic activity
OpenAlex ID: W4409873623