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Efficient copper-catalyzed cross-coupling of nitrogen nucleophiles with N,N-dibenzyl-4-iodobenzenesulfonamide and its application in the synthesis of Celecoxib intermediate
Citation
Yong, F.-F., Azri Miskal, Lim, D. Y.-E., & Teo, Y.-C. (2020). Efficient copper-catalyzed cross-coupling of nitrogen nucleophiles with N,N-dibenzyl-4-iodobenzenesulfonamide and its application in the synthesis of Celecoxib intermediate. Tetrahedron, 76(49), Article 131680. https://doi.org/10.1016/j.tet.2020.131680
Abstract
A practical and efficient strategy has been developed for the cross-coupling of N,N-dibenzyl-4-iodobenzenesulfonamide with nitrogen nucleophiles using 0.5–20 mol% of CuI under ligand-free conditions. A variety of nitrogen nucleophiles including nitrogen heterocycles, sulfonamides and amides afforded the corresponding products in moderate to good yields (up to 98%) under the optimized conditions. The application of this catalytic system to the synthesis of Celecoxib intermediate was also successfully demonstrated.
Date Issued
2020
Publisher
Elsevier
Journal
Tetrahedron
Grant ID
NIE Academic Research Fund
Funding Agency
National Institute of Education, Singapore