Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

• Published in: European journal of organic chemistry Vol. 2018; no. 2; pp. 150 - 159
• Main Authors: Mo, Xue‐Ling, Chen, Chun‐Hua, Liang, Cui, Mo, Dong‐Liang
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 17.01.2018; Wiley Subscription Services, Inc
• Subjects: Boron; Carbonyl groups; Carbonyls; Chemistry; Chemistry, Organic; Copper; Coupling; Cross‐coupling; Functional groups; Nitrogen heterocycles; Oximes; Physical Sciences; Science & Technology; Synthetic methods; OXIDATION; HYDROXYLAMINES; VINYL NITRONES; ARYLATION; EFFICIENT SYNTHESIS; BORONIC ACIDS; REARRANGEMENT; Boron; KETONITRONES; ETHERS; Cross-coupling; Nitrogen heterocycles; 1,3-DIPOLAR CYCLOADDITION; Synthetic methods; Copper
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201701324

A variety of (E)‐N‐aryloxindole nitrones were prepared in good to excellent yields by using a copper‐catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)‐oxindole nitrones. This method to prepare (E)‐N‐aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone‐derived oxindole nitrone in high yield. An efficient carbonyl group controlled strategy was developed to prepare (E)‐N‐arylisatin ketonitrones in good to excellent yields from the copper‐catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. DCE = 1,2‐dichloroethane.