A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents

Gabriele Grieco, Olivier Blacque and Heinz Berke
Beilstein J. Org. Chem. 2015, 11, 1656–1666. https://doi.org/10.3762/bjoc.11.182

Supporting Information

Supporting Information File 1: CIF file of compound 5.
Format: CIF Size: 32.4 KB Download
Supporting Information File 2: NMR and HRMS–ESI analyses.
Format: PDF Size: 1.3 MB Download

Cite the Following Article

A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents
Gabriele Grieco, Olivier Blacque and Heinz Berke
Beilstein J. Org. Chem. 2015, 11, 1656–1666. https://doi.org/10.3762/bjoc.11.182

How to Cite

Grieco, G.; Blacque, O.; Berke, H. Beilstein J. Org. Chem. 2015, 11, 1656–1666. doi:10.3762/bjoc.11.182

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Sosa-Rivadeneyra, M. V.; Rodríguez, J. C. P.; Torres, Y.; Bernès, S.; Percino, M. J.; Höpfl, H. Molecular crystals of 2-methyl-1H-benzo[d]imidazole and pyridine-2,6-dimethanol with chloranilic, trimesic and gallic acid. Journal of Molecular Structure 2024, 138118. doi:10.1016/j.molstruc.2024.138118
  • Silva Moratório de Moraes, R.; Tereza Miranda Martins, M.; Tavares de Almeida Pinto, G.; Couto Rodrigues, S.; Antunes do Nascimento, P.; Cardoso Cruz, C.; D'Oliveira Góes, K.; Claudia Cunha, A. An overview on generation and general properties of N-heterocyclic carbenes: Applications of 1,2,4-triazolium carbenes as metal free organocatalysts. Arabian Journal of Chemistry 2024, 17, 105527. doi:10.1016/j.arabjc.2023.105527
  • Marinho, E. One-Pot Reactions of Triethyl Orthoformate with Amines. Reactions 2023, 4, 779–800. doi:10.3390/reactions4040045
  • Khazipov, O. V.; Shepelenko, K. E.; Soliev, S. B.; Nikolaeva, K. A.; Chernyshev, V. M.; Ananikov, V. P. Optimal Balance in the Catalyst Dynamics Enables C(2)−H Arylation of (Benz)imidazoles and (Benz)oxazoles by an In Situ‐Generated Ni/NHC System. ChemCatChem 2022, 14. doi:10.1002/cctc.202201055
  • Chesnokov, V. V.; Shevchenko, M. A.; Astakhov, A. V. A study of the reactivity and transformations of Pd/NHC complexes in the reaction of oxidative C−H acetoxylation. Russian Chemical Bulletin 2022, 71, 1247–1256. doi:10.1007/s11172-022-3526-y
  • Chernyshev, V. M.; Khazipov, O. V.; Shevchenko, M. A.; Pasyukov, D. V.; Burykina, J. V.; Minyaev, M. E.; Eremin, D. B.; Ananikov, V. P. Discovery of the N–NHC Coupling Process under the Conditions of Pd/NHC- and Ni/NHC-Catalyzed Buchwald–Hartwig Amination. Organometallics 2022, 41, 1519–1531. doi:10.1021/acs.organomet.2c00166
  • Hamze, R.; Idris, M.; Ravinson, D. S. M.; Jung, M. C.; Haiges, R.; Djurovich, P. I.; Thompson, M. E. Highly Efficient Deep Blue Luminescence of 2-Coordinate Coinage Metal Complexes Bearing Bulky NHC Benzimidazolyl Carbene. Frontiers in chemistry 2020, 8, 401. doi:10.3389/fchem.2020.00401
  • Lin, T.-H.; Lee, G.-H.; Peng, S.-M.; Chiu, C.-W.; Chen, H.-Y. Benzannulated N-heterocyclic plumbylene: An efficient catalyst in ring opening polymerization of l-lactide. Polymer 2019, 180, 121748. doi:10.1016/j.polymer.2019.121748
  • Grieco, G.; Blacque, O. Solution and Solid‐State Structure of the First NHC‐Substituted Rhenium Heptahydrides. European Journal of Inorganic Chemistry 2019, 2019, 3810–3819. doi:10.1002/ejic.201900712
  • Nomiya, K.; Murata, Y.; Iwasaki, Y.; Arai, H.; Takuya, Y.; Kasuga, N. C.; Matsubara, T. Dataset of polyoxometalate-assisted N-heterocyclic carbene gold(I) complexes. Data in brief 2019, 25, 104002. doi:10.1016/j.dib.2019.104002
  • Nomiya, K.; Murara, Y.; Iwasaki, Y.; Arai, H.; Takuya, Y.; Kasuga, N. C.; Matsubara, T. Highly active, homogeneous catalysis by polyoxometalate-assisted N-heterocyclic carbene gold(I) complexes for hydration of diphenylacetylene. Molecular Catalysis 2019, 469, 144–154. doi:10.1016/j.mcat.2019.02.014
  • Paul, M.; Sudkaow, P.; Wessels, A.; Schlörer, N.; Neudörfl, J.-M.; Berkessel, A. Breslow‐Intermediate aromatischer N‐heterocyclischer Carbene (Benzimidazolin‐2‐ylidene, Thiazolin‐2‐ylidene). Angewandte Chemie 2018, 130, 8443–8448. doi:10.1002/ange.201801676
  • Paul, M.; Sudkaow, P.; Wessels, A.; Schlörer, N.; Neudörfl, J.-M.; Berkessel, A. Breslow Intermediates from Aromatic N-Heterocyclic Carbenes (Benzimidazolin-2-ylidenes, Thiazolin-2-ylidenes). Angewandte Chemie (International ed. in English) 2018, 57, 8310–8315. doi:10.1002/anie.201801676
  • Grieco, G.; Blacque, O.; Berke, H. A Facile Synthetic Route to Benzimidazolium Salts Bearing Bulky Aromatic N-Substituents. ChemInform 2015, 46. doi:10.1002/chin.201548146

Patents

  • DONG KAIWU; YAO QIYI; SHEN CHAOREN; ZHANG HONGRU; XU ZHENGSHUAI; JI XIAOLEI; SHI ZHANGLIN; TANG LIN. Imidazole ligand derivative as well as preparation and application thereof in butadiene telomerization reaction. CN 113801161 A, Dec 17, 2021.
Other Beilstein-Institut Open Science Activities