A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene

An isolable ring-fused pyridinylidene (a so-called Hammick intermediate) was synthesized from a benzo[<i>h</i>]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<sub>carbene</sub> interaction. Additionally, an example of isomerization of a carbene into another carbene, namely, a benzo[<i>h</i>]isoquinolin-1-ylidene into a benzo[<i>h</i>]isoquinolin-3-ylidene, is reported.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-04-28
DOI
https://doi.org/10.1021/jacs.5c05642
Citations
7
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
6.55

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article

A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene

Milan Gembický, Guy Bertrand, Olivier Baslé, Jakub Talcik et al.
7 citations
Journal of the American Chemical Society
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
6.55
article

A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene

Milan Gembický, Guy Bertrand, Olivier Baslé, Jakub Talcik, Marc Mauduit, Jan Lorkowski, Rodolphe Jazzar, Delphine Pichon, Patrick Yorkgitis, Levan Gojiashvili, Thierry Roisnel
article en
7 citations

Abstract

An isolable ring-fused pyridinylidene (a so-called Hammick intermediate) was synthesized from a benzo[<i>h</i>]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<sub>carbene</sub> interaction. Additionally, an example of isomerization of a carbene into another carbene, namely, a benzo[<i>h</i>]isoquinolin-1-ylidene into a benzo[<i>h</i>]isoquinolin-3-ylidene, is reported.

Journal of the American Chemical SocietyVol. 147(18)
Centre National de la Recherche Scientifique (FR), University of California San Diego (US), École Nationale Supérieure de Chimie de Rennes (FR), Laboratoire de Chimie de Coordination (FR), Université de Rennes (FR)
National Science Foundation, Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, Division of Chemistry
Openalex Percentile: Top 3%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
6.55
DOIOpen Access PDFOpenAlex
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A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene — Milan Gembický, Guy Bertrand, et al. · Journal of the American Chemical Society (2025) | TGRS Research Map | TGRS