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CONCURRENT PATHWAY AND UNEXPECTED PRODUCTS IN THE CuAAC REACTION OF ETHYL PROP-2-YNYL METHYLPHOSPHONATE WITH AROMATIC AZIDES

Nazariy T. Pokhodylo, Olga Ya. Shyyka, Mykola A. Tupychak, Yurii I. Slyvka, Mykola D. Obushak
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Abstract


The CuI-mediated click reaction of aromatic azides, containing the carboxyl moiety in the ortho position to the azido group, with ethylprop-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.

Keywords


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

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