An Optimized Ni-catalyzed Chan-Lam Type Coupling: Enantioretentive Access to Chiral N-Aryl Sulfinamides |
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Authors: | Chen Li Kun Zhang Hongrui Ma Shuang Wu Yilei Huang Yafei Duan Yunhao Luo Prof. Jun Yan Prof. Guang Yang |
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Affiliation: | 1. The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University., No. 38 Tongyan Road, Jinnan District, Tianjin, 300350 P. R. of China These authors contributed equally.;2. The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University., No. 38 Tongyan Road, Jinnan District, Tianjin, 300350 P. R. of China;3. School of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan Province, 410083 P. R. of China |
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Abstract: | C−N bond formation takes on a critical significance in reactions of organic synthesis, material production and pharmaceutical manufactory. Chan-Lam has proposed a useful methodology to furnish secondary arylamides under mild conditions. However, when chiral sulfinamides serve as the coupling precursors, the Cu-catalyzed coupling reaction is found with low efficacy. Complex side-products are generated under classic conditions. Moreover, it led to the racemization of the coupling product. In this study, an optimized Ni-catalyzed Chan-Lam type coupling conditions were proposed, which resulted in clean conversion from chiral sulfinamides and arylboronic acids to offer N-aryl sulfinamides efficiently and enantioretentively. The trans-N1,N2-dimethylcyclohexane-1,2-diamine was proven as the most efficient ligand. Under the optimized conditions, a series of chiral N-aryl sulfinamides was prepared with high chemical yield without racemization. Furthermore, a plausible and novel mechanism was proposed. Interestingly, the method could efficiently furnish a wide variety of C−X bonds by coupling arylboronic acids with different nucleophiles. |
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Keywords: | chiral N-aryl Sulfinamide C−X bonds formation enantioretention ni-catalyzed chan-lam type coupling |
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