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Palladium-Catalyzed C–N Cross Coupling of Sulfinamides and Aryl Halides

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journal contribution
posted on 04.05.2012, 00:00 by Xiaofei Sun, Xingzhao Tu, Chuan Dai, Xiaoping Zhang, Binbin Zhang, Qingle Zeng
The palladium-catalyzed C–N cross coupling of sulfinamides and aryl halides is reported. In the presence of Pd2(dba)3, tBuXPhos, NaOH, and a small amount of water, the C–N cross coupling of chiral tert-butanesulfinamide and aryl halides was accomplished to give N-aryl tert-butanesulfinamide without racemization, and the coupling of racemic p-toluenesulfinamide smoothly afforded N-aryl p-toluenesulfinamides. 2-Bromopyridine was also suitable for the coupling. Addition of a small amount of water to the catalytic system was of importance to obtain high yields.

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