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

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

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

页码：9543 / 9547

页数：5

共 54 条

[1] Pd/Cu-Catalyzed Enantioselective Sequential Heck/Sonogashira Coupling: Asymmetric Synthesis of Oxindoles Containing Trifluoromethylated Quaternary Stereogenic Centers [J].

Bai, Xingfeng ;

Wu, Caizhi ;

Ge, Shaozhong ;

Lu, Yixin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (07) :2764-2768

[2] Stereoselective synthesis and applications of spirocyclic oxindoles [J].

Boddy, Alexander J. ;

Bull, James A. .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (05) :1026-1084

[3] Role of estrone on the regulation of osteoblastogenesis [J].

Carla Crescitelli, M. ;

Belen Rauschemberger, M. ;

Cepeda, Sabrina ;

Sandoval, Marisa ;

Massheimer, Virginia L. .

MOLECULAR AND CELLULAR ENDOCRINOLOGY, 2019, 498

[4] Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles [J].

Chen, Jia-Rong ;

Yu, Xiao-Ye ;

Xiao, Wen-Jing .

SYNTHESIS-STUTTGART, 2015, 47 (05) :604-629

[5] Copper-catalyzed enantioselective arylboronation of activated alkenes leading to chiral 3,3′-disubstituted oxindoles [J].

Chen, Jiangfei ;

Li, Jin-Heng ;

Zhu, Yan-Ping ;

Wang, Qiu-An .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (11) :2532-2536

[6] Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine [J].

Chen, Ming ;

Wang, Xucai ;

Yang, Pengfei ;

Kou, Xun ;

Ren, Zhi-Hui ;

Guan, Zheng-Hui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :12199-12205

[7] Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes [J].

Cheung, Chi Wai ;

Ma, Jun-An ;

Hu, Xile .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (22) :6789-6792

[8] Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes [J].

Cheung, Chi Wai ;

Ploeger, Marten Leendert ;

Hu, Xile .

CHEMICAL SCIENCE, 2018, 9 (03) :655-659

[9] Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines [J].

Correia, Valquirio G. ;

Abreu, Juliana C. ;

Barata, Caio A. E. ;

Andrade, Leandro H. .

ORGANIC LETTERS, 2017, 19 (05) :1060-1063

[10] Catalytic asymmetric synthesis of hetero-substituted oxindoles [J].

Dalpozzo, Renato .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10) :2063-2078

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