Abstract
Asymmetric synthesis of enantioenriched azo compounds bearing tetrasubstituted stereocenter was achieved through chiral N,N′-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction of aryldiazonium tetrafluoroborate salts with nucleophiles under mild conditions. This protocol features wide substrate scope and good functional group compatibility. Azaarene-containing chiral azo compounds were stable enough in Japp-Klingemann reaction condition. The key to success of the reaction was the employment of metal salt/N,N′-dioxide ligand and the dual-task roles of the base. Moreover, the X-ray crystal structure of Ni(II)/N,N′-dioxide/substrate complex confirmed that the substrate was activated by bidentate coordination, which shed light on the origin of chiral control of the reaction.
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Acknowledgements
This work was supported by the National Natural Science Foundation of China (21890723, 21921002).
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Catalytic asymmetric synthesis of chiral azo compounds via interrupted Japp-Klingemann reaction with aryldiazonium salts
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Wang, Y., Yihuo, A., Wang, L. et al. Catalytic asymmetric synthesis of chiral azo compounds via interrupted Japp-Klingemann reaction with aryldiazonium salts. Sci. China Chem. 65, 546–553 (2022). https://doi.org/10.1007/s11426-021-1149-1
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DOI: https://doi.org/10.1007/s11426-021-1149-1