Sonogashira–Hagihara reactions of halogenated glycals

Dennis C. Koester and Daniel B. Werz
Beilstein J. Org. Chem. 2012, 8, 675–682.

Supporting Information

Supporting Information containing all experimental details and analytical data of all new compounds given in this article as well as their 1H and 13C NMR spectra is provided.

Supporting Information File 1: Experimental procedures, analytical data and NMR spectra.
Format: PDF Size: 2.7 MB Download

Cite the Following Article

Sonogashira–Hagihara reactions of halogenated glycals
Dennis C. Koester and Daniel B. Werz
Beilstein J. Org. Chem. 2012, 8, 675–682.

How to Cite

Koester, D. C.; Werz, D. B. Beilstein J. Org. Chem. 2012, 8, 675–682. doi:10.3762/bjoc.8.75

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

  • Paschoalin, C.; Toledo, M. F. Z. J.; Veríssimo, D.; Hornink, M. M.; Pimenta, D. C.; Stefani, H. A. Synthesis of Gluco‐Alkynones via a Carbonylative Coupling Reaction Using 1‐Iodoglucal. ChemistrySelect 2023, 8. doi:10.1002/slct.202303225
  • Correia, J. T. M.; Paixão, M. W.; de Souza, W. C.; Lima, R. N.; de Jesus, I. S. Synthesis of Benzoazepinone Derivatives via Photoredox Deaminative Radical Cascade Alkylation of 1,7-Dienes and 1,7-Enynes. Synthesis 2022, 55, 967–976. doi:10.1055/a-1953-1849
  • Godlewski, B.; Baran, D.; de Robichon, M.; Ferry, A.; Ostrowski, S.; Malinowski, M. Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins. Organic Chemistry Frontiers 2022, 9, 2396–2404. doi:10.1039/d1qo01909k
  • Luo, Z.-X.; Liu, M.; Li, T.; Xiong, D.-C.; Ye, X.-S. Electrochemical Bromination of Glycals. Frontiers in chemistry 2021, 9, 796690. doi:10.3389/fchem.2021.796690
  • Agrahari, A. K.; Bose, P.; Jaiswal, M. K.; Rajkhowa, S.; Singh, A. S.; Hotha, S.; Mishra, N.; Tiwari, V. K. Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications. Chemical reviews 2021, 121, 7638–7956. doi:10.1021/acs.chemrev.0c00920
  • Singh, A. K.; Kanaujiya, V. K.; Tiwari, V.; Sabiah, S.; Kandasamy, J. Development of Routes for the Stereoselective Preparation of β-Aryl-C-glycosides via C-1 Aryl Enones. Organic letters 2020, 22, 7650–7655. doi:10.1021/acs.orglett.0c02843
  • Rojas, A. H.; Lafuente, L.; Echeverría, G. A.; Piro, O. E.; Vetere, V.; Ponzinibbio, A. Synthesis and structure of novel iodinated N-glycosyl-sulfonamides through Aza-Ferrier reaction of 2-substituted glycals. Tetrahedron Letters 2020, 61, 152282. doi:10.1016/j.tetlet.2020.152282
  • Shelke, Y. G.; Yashmeen, A.; Gholap, A.; Gharpure, S. J.; Kapdi, A. R. Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules. Chemistry, an Asian journal 2018, 13, 2991–3013. doi:10.1002/asia.201801020
  • Singh, A. K.; Kandasamy, J. Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature. Organic & biomolecular chemistry 2018, 16, 5107–5112. doi:10.1039/c8ob01393d
  • Choutka, J.; Pohl, R.; Parkan, K. MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals. ACS omega 2018, 3, 7875–7887. doi:10.1021/acsomega.8b00901
  • Liao, H.; Ma, J.; Yao, H.; Liu, X.-W. Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals. Organic & biomolecular chemistry 2018, 16, 1791–1806. doi:10.1039/c8ob00032h
  • Bayón, C.; He, N.; Deir‐Kaspar, M.; Blasco, P. D.; André, S.; Gabius, H.-J.; Rumbero, Á.; Jiménez-Barbero, J.; Fessner, W.-D.; Hernáiz, M. J. Direct Enzymatic Branch-End Extension of Glycocluster-Presented Glycans: An Effective Strategy for Programming Glycan Bioactivity. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 23, 1623–1633. doi:10.1002/chem.201604550
  • Bordessa, A.; Ferry, A.; Lubin-Germain, N. Access to Complex C2-Branched Glycoconjugates via Palladium-Catalyzed Aminocarbonylation Reaction of 2-Iodoglycals. The Journal of organic chemistry 2016, 81, 12459–12465. doi:10.1021/acs.joc.6b02278
  • Li, X.; Zhu, J. Glycosylation via Transition‐Metal Catalysis: Challenges and Opportunities. European Journal of Organic Chemistry 2016, 2016, 4724–4767. doi:10.1002/ejoc.201600484
  • Ievlev, M. Y.; Ershov, O. V.; Belikov, M. Y.; Milovidova, A. G.; Tafeenko, V. A.; Nasakin, O. E. Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group. Beilstein journal of organic chemistry 2016, 12, 2093–2098. doi:10.3762/bjoc.12.198
  • Tatina, M. B.; Hussain, A.; Dhas, A. K.; Mukherjee, D. Advances in C-alkynylation of sugars and its application in organic synthesis. RSC Adv. 2016, 6, 75960–75972. doi:10.1039/c6ra11672h
  • Pradhan, S.; Dutta, S.; John, R. P. A coordination driven self-assembled Pd6L8 nanoball catalyses copper and phosphine-free Sonogashira coupling reaction in both homogeneous and heterogeneous formats. New Journal of Chemistry 2016, 40, 7140–7147. doi:10.1039/c5nj03658e
  • Vankar, Y. D.; Linker, T. Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates. European Journal of Organic Chemistry 2015, 2015, 7633–7642. doi:10.1002/ejoc.201501176
  • Shamim, A.; Vasconcelos, S. N. S.; Ali, B.; Madureira, L. S.; Zukerman-Schpector, J.; Stefani, H. A. Ligand and copper free Sonogashira coupling to achieve 2-alkynyl d-glucal derivatives: regioselective electrophile promoted nucleophilic 5-endo-dig cyclization. Tetrahedron Letters 2015, 56, 5836–5842. doi:10.1016/j.tetlet.2015.08.052
  • Oroszová, B.; Choutka, J.; Pohl, R.; Parkan, K. Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp2–sp3 Suzuki–Miyaura Reaction. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 7043–7047. doi:10.1002/chem.201406591
Other Beilstein-Institut Open Science Activities