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Rh(III)-Catalyzed Atroposelective C-H Cyanation of 1-Aryl benzo[h]isoquinolines
Dong-Song Zheng1, Bo-Bo Gou1, Fangnuo Zhao1
1New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Abstract:
The atroposelective C-H cyanation of 1-aryl isoquinolines using rhodium(III) catalysis was realized. In the presence of a chiral binaphthyl "O"-linked Cp rhodium (BOCpRh) complex, highly atroposelective C-H cyanation of 1-aryl isoquinolines with N-cyano-N-phenyl-p-toluenesulfonamide proceeded smoothly to afford a wide range of axially chiral 1-aryl isoquinoline nitriles in up to 94% yield and 91% ee. This method provides a facile access to axially chiral nitriles under mild conditions. The transformations of the products and preliminary mechanistic studies have been carried out.
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