Diaryl amines are becoming ever more useful intermediates in many applications such as drugs, photoelectric materials, etc. Amination of aryl halides with aryl amines have been reported with the use of palladium catalysts with an array of ligands.1 Aryl fluorosulfonates can be prepared in quantitative yields from the reaction of phenol derivatives and sulfuryl fluoride, and we tested if aryl fluorosulfonates could be applied as alternative cross-coupling partners to aryl halides in palladium-catalyzed aminations.2
We report the direct amination of aryl fluorosulfonates with arylamines using Pd(0) catalysts. This Buchwald-Hartwig type amination occurs under mild conditions in the presence of Pd(PPh3)4, without any additional N- or P-type ligand. This protocol provides a quite straightforward alternative for the amination of aryl amines, using aryl sulfonates instead of aryl halides.
1. John P. Wolfe and Stephen L. Buchwald, J. Org. Chem. 1997, 62, 1264-1267
2. Qiaobin Liang, Ping Xing, Zuogang Huang, Jiajia Dong, K. Barry Sharpless, Xiaoxian Li, and Biao Jiang, Org. Lett. 2015, 17, 1942−1945