Nickel-Catalyzed Arylcarbamoylation of Alkenes of N-(o-lodoaryl)acrylamides with Nitroarenes via Reductive Aminocarbonylation: Facile Synthesis of Carbamoyl-Substituted Oxindoles

被引:23
作者
Cheng, Chaozhihui [1 ,2 ]
Xiang, Jian-Nan [1 ]
Zhu, Yan-Ping [3 ]
Peng, Zhi-Hong [1 ]
Li, Jin-Heng [1 ,2 ,3 ,4 ]
机构
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China
[2] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China
[3] Yantai Univ, Collaborat Innovat Ctr Adv Drug Delivery Syst & B, Sch Pharm, Key Lab Mol Pharmacol & Drug Evaluat,Minist Educ, Yantai 264005, Shandong, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 475004, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
H FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.1c03762
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nickel-catalyzed arylcarbamoylation reactions of alkenes of N- o-haloaryl)acrylarnides with CO and nitroarenes via reductive aminocarbonylation to produce carbamoyl-substituted oxindoles with an all-carbon quaternary stereogenic center are presented. Starting with N-(o-haloaryl)acrylamides, simple CO, and inexpensive nitroarenes and using a Ni catalyst, a dinitrogen-based ligand, a Zn reductant, a TMSCI additive, and a base system, this protocol enables the synthesis of various carbamoyl-substituted oxindoles and allows the efficient late-stage derivatization of valuable molecules.
引用
收藏
页码:9543 / 9547
页数:5
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