Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

Adrián A. Heredia and Alicia B. Peñéñory
Beilstein J. Org. Chem. 2017, 13, 910–918. https://doi.org/10.3762/bjoc.13.92

Supporting Information

Supporting Information File 1: Experimental details, characterization data and copies of 1H, 13C and 77Se NMR spectra for products 5ae, 5il, 5n, 5q, 9 and 10.
Format: PDF Size: 2.7 MB Download

Cite the Following Article

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions
Adrián A. Heredia and Alicia B. Peñéñory
Beilstein J. Org. Chem. 2017, 13, 910–918. https://doi.org/10.3762/bjoc.13.92

How to Cite

Heredia, A. A.; Peñéñory, A. B. Beilstein J. Org. Chem. 2017, 13, 910–918. doi:10.3762/bjoc.13.92

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: 750.6 KB Download

Citations to This Article

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

Scholarly Works

  • Andreev, M. V.; Potapov, V. A.; Musalov, M. V.; Larina, L. I. A New Family of Vinyl Selenocyanates with the Amide Function Based on the Reaction of Potassium Selenocyanate with 3-Trimethylsilyl-2-Propynamides. Catalysts 2023, 13, 1257. doi:10.3390/catal13091257
  • Wu, G.; Zhou, X.; Wang, C. Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids. Chinese Chemical Letters 2022, 33, 4531–4535. doi:10.1016/j.cclet.2022.01.044
  • Shaaban, S.; El-Lateef, H. M. A.; Khalaf, M. M.; Gouda, M.; Youssef, I. One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds. Polymers 2022, 14, 2208. doi:10.3390/polym14112208
  • Lalithamba, H. S.; Raghavendra, M.; Yatish, K. V. Efficient Application of Green Synthesized CeO2 Nanoparticles for the Preparation of Selenoester Derivatives of Protected Amino Acids and Production of Biodiesel from Annona squamosa Oil. Journal of Electronic Materials 2022, 51, 3650–3659. doi:10.1007/s11664-022-09610-x
  • Thurow, S.; Abenante, L.; Anghinoni, J. M.; Lenardão, E. J. Selenium as a Versatile Reagent in Organic Synthesis: More than Allylic Oxidation. Current organic synthesis 2022, 19, 331–365. doi:10.2174/1570179418666210525152001
  • Marini, F.; Bagnoli, L.; Palomba, M. Synthesis of organochalcogens: use of nonconventional solvents/reaction media. Organochalcogen Compounds; Elsevier, 2022; pp 147–192. doi:10.1016/b978-0-12-819449-2.00005-7
  • Manna, T.; Rana, A.; Misra, A. K. Synthesis of unsymmetrical glycosyl diselenides by the treatment of symmetrical diselenides with glycosyl selenocyanates. Tetrahedron 2021, 95, 132358. doi:10.1016/j.tet.2021.132358
  • Sonawane, A. D.; Sonawane, R. A.; Ninomiya, M.; Koketsu, M. Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms. Advanced Synthesis & Catalysis 2020, 362, 3485–3515. doi:10.1002/adsc.202000490
  • Wang, D.-L.; Fang, Y.; Wang, S.-Y.; Ji, S.-J. Silver-mediated activation of terminal alkynes: A strategy to construct bis-ethynynl selenides and tellurides. Tetrahedron 2020, 76, 131083. doi:10.1016/j.tet.2020.131083
  • Manna, T.; Misra, A. K. Glycosyl selenoacetates: versatile building blocks for the preparation of stereoselective selenoglycosides and selenium linked disaccharides. Organic & biomolecular chemistry 2019, 17, 8902–8912. doi:10.1039/c9ob01623f
  • Coelho, F. L.; Dresch, L. C.; Stieler, R.; Campo, L. F.; Schneider, P. H. New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for CSe and CS coupling reactions. Catalysis Communications 2019, 121, 19–26. doi:10.1016/j.catcom.2018.12.009
  • Sano, R.; Kudo, A.; Tsubogo, T.; Uchiro, H. Phenylselenylation of Ethers using Diphenyl Diselenide–Tributylphosphine–Molecular Oxygen System under Mild Reaction Conditions. Asian Journal of Organic Chemistry 2018, 7, 724–728. doi:10.1002/ajoc.201800026
Other Beilstein-Institut Open Science Activities