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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
Tetrahedron ( IF 2.1 ) Pub Date : 2020-10-17 , DOI: 10.1016/j.tet.2020.131680
Fui-Fong Yong , Miskal Azri , Yong-En Darrell Lim , Yong-Chua Teo

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.



中文翻译:

氮亲核试剂与N,N-二苄基-4-碘代苯磺酰胺的铜催化高效交叉偶联及其在塞来昔布中间体合成中的应用

已经开发了一种实用且有效的策略,用于在无配体条件下使用0.5–20 mol%的CuI将N,N-二苄基-4-碘代苯磺酰胺与N亲核试剂交叉偶联。在优化的条件下,包括氮杂环,磺酰胺和酰胺在内的各种氮亲核试剂以中等至良好的收率(高达98%)提供了相应的产品。还成功证明了该催化体系在塞来昔布中间体合成中的应用。

更新日期:2020-11-12
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