1. Nickel(II)-catalyzed addition reaction of arylboronic acids to isatins
- Author
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Xuefeng He, Huixuan Chen, Liqin Qiu, Xiangmeng Chen, Xiaoding Jiang, Yaqi Zhang, Wenhuan He, Yongsu Li, Hao Liang, and Yuyang Zhang
- Subjects
Addition reaction ,010405 organic chemistry ,Ligand ,Organic Chemistry ,Enantioselective synthesis ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Catalysis ,Nickel ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Drug Discovery ,Phosphine - Abstract
A Ni-catalyzed addition of arylboronic acids to isatins was first developed. The reaction, driven by Ni(acac)2 and dppp as the phosphine ligand, gave 3-aryl-3-hydroxy-2-oxindoles in up to 97% yield. Scopes of benzyl-protected isatins and arylboronic acids were examined. Substituted phenylboronic acids along with fused-ring and heterocyclic boronic acids reacted with isatins smoothly. Preliminary asymmetric catalysis was investigated as well, showing moderate enantioselectivity. The mechanism was also described.
- Published
- 2018
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