Nickel(II)-catalyzed addition reaction of arylboronic acids to isatins

• Published in: Tetrahedron Vol. 74; no. 18; pp. 2245 - 2250
• Main Authors: Zhang, Yu-Yang, Chen, Huixuan, Jiang, Xiaoding, Liang, Hao, He, Xuefeng, Zhang, Yaqi, Chen, Xiangmeng, He, Wenhuan, Li, Yongsu, Qiu, Liqin
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.05.2018; Elsevier
• Subjects: acids; Addition reaction; Boronic acids; catalytic activity; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; enantioselectivity; heterocyclic compounds; Isatins; ligands; nickel; Nickel catalysis; phenylboronic acids; phosphine; Physical Sciences; Science & Technology; Isatins; Addition reaction; Nickel catalysis; Boronic acids; PALLADIUM; GROWTH-HORMONE SECRETAGOGUES; SUZUKI CROSS-COUPLINGS; ALKYLATION; CARBONYL-COMPOUNDS; ALDEHYDES; CATALYZED ASYMMETRIC ADDITION; ENANTIOSELECTIVE ALKENYLATION; LIGANDS; ELECTROPHILES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2018.03.039

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. A Ni-catalyzed addition of arylboronic acids to isatins was first developed. The reaction, driven by Ni(acac)2 and dppp, gave 3-aryl-3-hydroxy-2-oxindoles in up to 97% yield. Substituted phenylboronic acids along with fused-ring and heterocyclic boronic acids reacted with isatins smoothly. [Display omitted]