Towards Structurally Versatile Mesoionic N-Heterocyclic Olefin Ligands and their Coordination to Palladium, Gold, and Boron Hydride DOI Creative Commons

Tisa Ževart,

Balázs Pintér, Matic Lozinšek

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(21), С. 8915 - 8925

Опубликована: Янв. 1, 2024

Coordination of 1,2,3-triazole-based mesoionic N-heterocyclic olefin (mNHO) ligands to palladium, gold, and boron hydride has been investigated experimentally computationally.

Язык: Английский

Sulfonyl-stabilized 4-alkylidene dihydropyridines as C-donor ligands in organotransition metal catalysis: Synthesis of palladium complexes DOI

Anushree Poddar,

F. Christopher Pigge

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134540 - 134540

Опубликована: Фев. 1, 2025

Язык: Английский

Процитировано

0
N-Heterocyclic Olefins of Pyrazole and Indazole DOI Creative Commons
Bolin Zhu,

Rouven Woyciechowski,

Eike G. Hübner

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

Deprotonation of 3-methylpyrazolium and 3-methylindazolium salts yielded N-heterocyclic olefins (NHOs) in excellent yields, which reacted with isocyanates, halogens, carbon disulfide. Calculated proton affinities are 261 kcal/mol (indazole NHOs) 272 (pyrazole NHOs). The calculated pKa values between 14.8 25.2, bond lengths the exocyclic double slightly shorter than those imidazole NHOs. As expected, highest occupied molecular orbitals show significant atomic orbital coefficients at atom.

Язык: Английский

Процитировано

0
2‐Methylene‐1,2‐dihydropyridines (2‐pyNHOs): Highly Nucleophilic Enamines DOI Creative Commons

Annika Behnke,

Andreas Eitzinger,

Yijie He

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(39)

Опубликована: Апрель 30, 2024

Abstract The high reactivity of 2‐methylene‐1,2‐dihydropyridines also known as 2‐methylpyridinium derived N ‐heterocyclic olefins (2‐pyNHOs) has been recognized in organic synthesis, yet a quantification their nucleophilicity is lacking. Herein we used stopped‐flow photometry to determine the series 2‐pyNHOs from kinetics reactions with quinone methides and benzhydrylium ions reference electrophiles four solvents at 20 °C. kinetic data was evaluated by using Mayr‐Patz equation, lg k (20 °C)= s ( + E ), which gave parameters (and ). With range 19.4–21.2 (in DMSO), exceed classical enamines, such pyrrolidino‐cyclopent‐1‐ene. addition resulted formation zwitterionic adducts pyridinium phenolate moieties. Subsequent tautomerization yielded entirely neutral pyridine‐2(1 H )‐ylidene‐phenol species several cases. Formation almost equally fast polar acetonitrile DMSO, but proceeded one two orders magnitude slower less dichloromethane or THF.

Язык: Английский

Процитировано

1
An Acceptor-Substituted N-Heterocyclic ortho-Quinodimethane: Pushing the Boundaries of Polarization in Donor–Acceptor-Substituted Polyenes DOI
Jama Ariai, Urs Gellrich

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(47), С. 32859 - 32869

Опубликована: Ноя. 14, 2024

We report the synthesis, isolation, and characterization of a stable donor-acceptor substituted

Язык: Английский

Процитировано

1
In-Depth Quantitative and Theoretical Study of Ambident Electrophilies of 2-Bromo-3-X-5-nitrothiophenes DOI

Amira Ghabi,

Rim Hamdi,

Rania Khaldi

и другие.

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 140106 - 140106

Опубликована: Сен. 1, 2024

Язык: Английский

Процитировано

0
Towards Structurally Versatile Mesoionic N-Heterocyclic Olefin Ligands and their Coordination to Palladium, Gold, and Boron Hydride DOI Creative Commons

Tisa Ževart,

Balázs Pintér, Matic Lozinšek

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(21), С. 8915 - 8925

Опубликована: Янв. 1, 2024

Coordination of 1,2,3-triazole-based mesoionic N-heterocyclic olefin (mNHO) ligands to palladium, gold, and boron hydride has been investigated experimentally computationally.

Язык: Английский

Процитировано

0