Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 374–378 | Cite as

Concurrent pathway and unexpected products in the CuAAC reaction of ethyl prop-2-ynyl methylphosphonate with aromatic azides

  • Nazariy T. PokhodyloEmail author
  • Olga Ya. Shyyka
  • Mykola A. Tupychak
  • Yurii I. Slyvka
  • Mykola D. Obushak

The CuI-mediated click reaction of aromatic azides, containing the carboxyl moiety in the ortho position to the azido group, with ethyl prop-2-ynyl methylphosphonate proceeded via a concurrent pathway whereby the formation of acrylamides predominated over "classical" cycloaddition products 1,2,3-triazoles. The reaction appears to be specific toward the ortho-carboxyl-substituted aromatic azides, while aryl azides with other substituents do not give the "reduction" products, but form the expected click products: (1-aryl-1H-1,2,3-triazol-4-yl)methyl ethyl methylphosphonates. The reaction mechanism is discussed.


azides phosphonates 1,2,3-triazoles click reaction unexpected product 



The authors are grateful to the Ministry of Education and Science of Ukraine for financial support of this work (grant No. 0118U003610).


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nazariy T. Pokhodylo
    • 1
    Email author
  • Olga Ya. Shyyka
    • 1
  • Mykola A. Tupychak
    • 1
  • Yurii I. Slyvka
    • 1
  • Mykola D. Obushak
    • 1
  1. 1.Department of Organic ChemistryIvan Franko National University of LvivLvivUkraine

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