Click and bio-orthogonal reactions with mesoionic compounds

K Porte, M Riomet, C Figliola, D Audisio… - Chemical …, 2020 - ACS Publications
Click and bio-orthogonal reactions are dominated by cycloaddition reactions in general and
1, 3-dipolar cycloadditions in particular. Among the dipoles routinely used for click chemistry …

Type A mesoionic compounds (1980–2020)

CA Ramsden, F Dumitrascu - Advances in Heterocyclic Chemistry, 2022 - Elsevier
Type A mesoionic compounds are of particular interest due to their participation in
synthetically useful 1, 3-dipolar cycloaddition reactions. This review covers the chemistry of …

Influence of endo-and exocyclic heteroatoms on stabilities and 1, 3-dipolar cycloaddition reactivities of mesoionic azomethine ylides and imines

PA Champagne, KN Houk - The Journal of organic chemistry, 2017 - ACS Publications
The geometries, stabilities, and 1, 3-dipolar cycloaddition reactivities of 24 mesoionic
azomethine ylides and imines were investigated using density functional theory calculations …

Potential Energy Surfaces of HN(CH)SX:CO2 for X = F, Cl, NC, CN, CCH, and H: N···C Tetrel Bonds and O···S Chalcogen Bonds

JE Del Bene, I Alkorta, J Elguero - The Journal of Physical …, 2019 - ACS Publications
MP2/aug′-cc-pVTZ calculations have been performed in search of complexes, molecules,
and transition structures on the HN (CH) SX: CO2 potential energy surfaces, for X= F, Cl, NC …

Formation of N‐Heterocyclic Carbenes by Tautomerization of Mesomeric Betaines: Cyclic Boron Adducts and Palladium Complexes From 2‐(Imidazolium‐1‐yl) …

M Liu, M Nieger, EG Hübner… - Chemistry–A European …, 2016 - Wiley Online Library
(Imidazolium‐1‐yl) phenolates are conjugated heterocyclic mesomeric betaines in
tautomeric equilibrium with the corresponding N‐heterocyclic carbenes (NHCs), 3‐(2 …

[HTML][HTML] Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenes

T Freese, JC Namyslo, M Nieger, A Schmidt - RSC advances, 2019 - pubs.rsc.org
The sydnone imines (5-benzoylimino)-3-(2-methoxyphenyl)-sydnone imine and
molsidomine were deprotonated at C4 to give sydnone imine anions which can be …

Cycloadditions of anionic N-heterocyclic carbenes of sydnone imines

T Freese, M Nieger, JC Namyslo, A Schmidt - Tetrahedron letters, 2019 - Elsevier
Sydnone imines were deprotonated with lithium bis (trimethylsilyl) amide at the C4 position
to give the corresponding sydnone imine anions as lithium adducts. These can be …

Synthesis of mesoionic triazolones via a formal [3+ 2] cycloaddition between 4-phenyl-1, 2, 4-triazoline-3, 5-dione and alkynes

Y Kuroda, M Krell, K Kurokawa, K Takasu - Chemical Communications, 2024 - pubs.rsc.org
1, 2, 4-Triazoline-3, 5-diones (TADs) are versatile reagents and have found widespread
adoption in chemical science. Despite their remarkable reactivity toward a wide array of …

[HTML][HTML] Palladium complexes of anionic N-heterocyclic carbenes derived from sydnones in catalysis

AL Lücke, S Wiechmann, T Freese, Z Guan… - … für Naturforschung B, 2016 - degruyter.com
The anion of N-phenylsydnone, which can be generated on treatment of N-phenylsydnone
with cyanomethyllithium without decomposition, can be represented as tripolar zwitterionic …

[HTML][HTML] Purine-substituted imidazolium mesomeric betaines and their tautomeric N-heterocyclic carbenes. Formation of a cyclic borane adduct

J Zhang, EG Hübner, JC Namyslo, M Nieger… - Organic & …, 2018 - pubs.rsc.org
6-Chloropurine and 2, 6-dichloropurine were reacted with N1-substituted imidazoles to give
purin-6-yl substituted imidazolium salts, respectively. Deprotonation of the 1 …