New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

Pavel Nagorny and Zhankui Sun
Beilstein J. Org. Chem. 2016, 12, 2834–2848. https://doi.org/10.3762/bjoc.12.283

Cite the Following Article

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation
Pavel Nagorny and Zhankui Sun
Beilstein J. Org. Chem. 2016, 12, 2834–2848. https://doi.org/10.3762/bjoc.12.283

How to Cite

Nagorny, P.; Sun, Z. Beilstein J. Org. Chem. 2016, 12, 2834–2848. doi:10.3762/bjoc.12.283

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.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 141.6 KB Download

Citations to This Article

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

Scholarly Works

  • Yang, J.; Zhang, Y.; Wong, H.-C. F.; Huang, J.; Tse, Y.-L. S.; Yeung, Y.-Y. Design and Applications of Cyclopropenium Chalcogen Dihalides in Catalysis via C(sp3)–H···X Interactions. ACS Catalysis 2024, 14, 3018–3027. doi:10.1021/acscatal.4c00087
  • Yalduz, S.; Eyilcim, Ö.; Kılıç, N.; Gülyüz, S.; Denizoğlu, O.; Zorlu, Y.; Ertürk, E. High-Yielding Process for the Synthesis of Hydroxychloroquine under Concentrated Conditions: Nucleophilic Amination of Chloropyridines Promoted by Dimethyl Sulfoxide or Catalyzed by 3,5-Bis(trifluoromethyl)phenol. Organic Process Research & Development 2023, 28, 137–151. doi:10.1021/acs.oprd.3c00220
  • Leung, V. M.-Y.; Wong, H.-C. F.; Pook, C.-M.; Tse, Y.-L. S.; Yeung, Y.-Y. Trialkylphosphonium oxoborates as C(sp3)-H oxyanion holes and their application in catalytic chemoselective acetalization. Chemical science 2023, 14, 12684–12692. doi:10.1039/d3sc03081d
  • Li, Y.; Ge, Y.; Sun, R.; Yang, X.; Huang, S.; Dong, H.; Liu, Y.; Xue, H.; Ma, X.; Fu, H.; Chen, Z. Balancing Activity and Stability in Halogen-Bonding Catalysis: Iodopyridinium-Catalyzed One-Pot Synthesis of 2,3-Dihydropyridinones. The Journal of organic chemistry 2023, 88, 11069–11082. doi:10.1021/acs.joc.3c01028
  • Düfert, A. Organokatalyse. Organische Synthesemethoden; Springer Berlin Heidelberg, 2023; pp 789–845. doi:10.1007/978-3-662-65244-2_8
  • Hum, G.; Phang, S. J. I.; Ong, H. C.; León, F.; Quek, S.; Khoo, Y. X. J.; Li, C.; Li, Y.; Clegg, J. K.; Díaz, J.; Stuparu, M. C.; García, F. Main Group Molecular Switches with Swivel Bifurcated to Trifurcated Hydrogen Bond Mode of Action. Journal of the American Chemical Society 2023, 145, 12475–12486. doi:10.1021/jacs.2c12713
  • Davis, T. A.; Garza, A. B.; Miller, R. G.; Gardner, S. B.; Fuhrer, T. J.; Campbell, A. B. Thiourea-Catalyzed Amidation of Esters: A New Method for the Preparation of Amides. Letters in Organic Chemistry 2023, 20, 2–10. doi:10.2174/1570178619666220615144433
  • Wang, X.; Wang, Y.-N.; Pei, Z.; Li, S.-J.; Wei, D.; Lan, Y. N-Heterocyclic Carbene/Brønsted Acid Cooperatively Catalyzed Conversions of α, β-Unsaturated Carbonyls: Hydrogen Bond Donor/Acceptor-Electrophile/Nucleophile Combination Models. ACS Catalysis 2022, 13, 612–623. doi:10.1021/acscatal.2c05373
  • Zelenkov, L. E.; Ivanov, D. M.; Tyumentsev, I. A.; Izotova, Y. A.; Kukushkin, V. Y.; Bokach, N. A. Structure-Directing Interplay between Tetrel and Halogen Bonding in Co-Crystal of Lead(II) Diethyldithiocarbamate with Tetraiodoethylene. International journal of molecular sciences 2022, 23, 11870. doi:10.3390/ijms231911870
  • Kia, R.; Heshmatnia, F. Structural and theoretical exploring of noncovalent interactions in Chlorido- and Nitrito-rhenium(I) tricarbonyl complexes bearing 2,3-Butadiene-bis(2-nitrobenzylidene)hydrazine Ligand: Intramolecular Re–κ1-endo-ONO(lone pair)…π*(C O) interaction. Inorganica Chimica Acta 2022, 540, 121049. doi:10.1016/j.ica.2022.121049
  • Aliyarova, I. S.; Tupikina, E. Y.; Ivanov, D. M.; Kukushkin, V. Y. Metal-Involving Halogen Bonding Including Gold(I) as a Nucleophilic Partner. The Case of Isomorphic Dichloroaurate(I)·Halomethane Cocrystals. Inorganic chemistry 2022, 61, 2558–2567. doi:10.1021/acs.inorgchem.1c03482
  • Shirakawa, S. doi:10.1002/9783527830664.ch8
  • Cruz-Hernández, C.; Juaristi, E. On the synthesis of a novel chiral phosphorodiamidic acid containing the α-phenylethyl moiety: Insights in its conformation and reactivity. Synthesis 2021, 54, 3801–3808. doi:10.1055/a-1689-3626
  • Ivanov, D. M.; Bokach, N. A.; Kukushkin, V. Y.; Frontera, A. Metal Centers as Nucleophiles: Oxymoron of Halogen Bond-Involving Crystal Engineering. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 28, e202103173. doi:10.1002/chem.202103173
  • Yıldırım, A.; Kaya, Y.; Göker, M. Screening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffold. Carbohydrate research 2021, 510, 108458. doi:10.1016/j.carres.2021.108458
  • Weiss, R.; Golisano, T.; Pale, P.; Mamane, V. Insight into the Modes of Activation of Pyridinium and Bipyridinium Salts in Non-Covalent Organocatalysis. Advanced Synthesis & Catalysis 2021, 363, 4779–4788. doi:10.1002/adsc.202100865
  • Jin, T. Z.; Moores, A. Nanoparticles in Catalysis; Wiley, 2021; pp 139–157. doi:10.1002/9783527821761.ch7
  • Retini, M.; Bartoccini, F.; Zappia, G.; Piersanti, G. Novel, Chiral, and Enantiopure C2-Symmetric Thioureas Promote Asymmetric Protio-Pictet-Spengler Reactions by Anion-Binding Catalysis. European Journal of Organic Chemistry 2021, 2021, 825–829. doi:10.1002/ejoc.202001501
  • Katlenok, E. A.; Rozhkov, A. V.; Levin, O. V.; Haukka, M.; Kuznetsov, M. L.; Kukushkin, V. Y. Halogen Bonding Involving Palladium(II) as an XB Acceptor. Crystal Growth & Design 2020, 21, 1159–1177. doi:10.1021/acs.cgd.0c01474
  • Zhang, H.; Toy, P. H. Halogen Bond‐Catalyzed Friedel−Crafts Reactions of Furans Using a 2,2’‐Bipyridine‐Based Catalyst. Advanced Synthesis & Catalysis 2020, 363, 215–221. doi:10.1002/adsc.202001019
Other Beilstein-Institut Open Science Activities