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Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins

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posted on 17.07.2015, 00:00 by Yue Zhuang, Yuwei He, Zihong Zhou, Wang Xia, Chuyu Cheng, Meng Wang, Bin Chen, Zhongyuan Zhou, Jiyan Pang, Liqin Qiu
A series of novel chiral phosphoramidite ligands based on chiral-bridged biphenyl backbones have been prepared conveniently and characterized. The ligands complexed with [IrCodCl]2 provided the first iridium catalyst system for the asymmetric addition of arylboronic acids to N-protected isatins with high efficiency. When performed in THF/H2O at 80 °C with 2 equiv of the arylboronic acids, the transformations acquired good to excellent results (up to 98% yield and 95% ee).