Efficient copper-catalyzed cross-coupling of nitrogen nucleophiles with N,N-dibenzyl-4-iodobenzenesulfonamide and its application in the synthesis of Celecoxib intermediate

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. [Display omitted]