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Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Nidhi Mishra, Sumit K. Singh, Anoop S. Singh, Anand K. Agrahari and Vinod K. Tiwari*

*Department of Chemistry, Centre of Advanced Study, Institute of Science, Banaras Hindu University, Varanasi 221005, India, Email: tiwari_chemyahoo.co.in

N. Mishra, S. K. Singh, A. S. Singh, A. K Agrahari, V. K. Tiwari, J. Org. Chem., 2021, 86, 17890-17895.

DOI: 10.1021/acs.joc.1c02194



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Abstract

Glycosyl triazoles are efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling. The atmospheric oxygen in a sealed tube did not affect the coupling. In contrast, at room temperature, a very low loading of the catalytic system could produce excellent yields in Glaser coupling including homocoupling and heterocoupling.


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proposed mechanism



Key Words

Sonogashira coupling, Glaser coupling


ID: J42-Y2021