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Aza-Wacker-Type Reaction between Electron-Deficient Olefins and N‑Alkylsulfonamides

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journal contribution
posted on 06.03.2015, 00:00 by Huayou Hu, Jiaxin Tian, Yun Liu, Yong Liu, Fei Shi, Xiang Wang, Yuhe Kan, Chao Wang
A palladium-catalyzed oxidative amination protocol of electron-deficient olefins by aza-Wacker-type reaction with N-alkylsulfonamides was developed. The presence of the stoichiometric amount of methanesulfonic acid was crucial for the success of this transformation. The reactions were conducted in green solvent under mild conditions and scalable with excellent E-type stereoselectivity. In addition, a Pd­(II)/Pd(0) catalytic cycle with the existence of a very strong oxidant (Selectfluor) was proposed.