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

[21] Various difunctionalizations of acrylamide: an efficient approach to synthesize oxindoles [J].

Li, Chen-Chen ;

Yang, Shang-Dong .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (19) :4365-4377

[22] Ni-Catalyzed enantioselective reductive aryl-alkenylation of alkenes: application to the synthesis of (+)-physovenine and (+)-physostigmine [J].

Li, Yuxiu ;

Ding, Zhengtian ;

Lei, Aiwen ;

Kong, Wangqing .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18) :3305-3309

[23] 3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes [J].

Liang, Ren-Xiao ;

Chen, Ru-Yi ;

Zhong, Chao ;

Zhu, Jia-Wen ;

Cao, Zhong-Yan ;

Jia, Yi-Xia .

ORGANIC LETTERS, 2020, 22 (08) :3215-3218

[24] Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes [J].

Ling, Liang ;

Chen, Changpeng ;

Luo, Meiming ;

Zeng, Xiaoming .

ORGANIC LETTERS, 2019, 21 (06) :1912-1916

[25] Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1H)-ones [J].

Liu, Yongzhu ;

Qi, Xinxin ;

Wu, Xiao-Feng .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19) :13824-13832

[26] Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes [J].

Ma, Teng ;

Chen, Yate ;

Li, Yuxiu ;

Ping, Yuanyuan ;

Kong, Wangqing .

ACS CATALYSIS, 2019, 9 (10) :9127-9133

[27] Metal-Catalyzed Approaches toward the Oxindole Core [J].

Marchese, Austin D. ;

Larin, Egor M. ;

Mirabi, Bijan ;

Lautens, Mark .

ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (08) :1605-1619

[28] Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes [J].

Pan, Qi ;

Ping, Yuanyuan ;

Wang, Yifan ;

Guo, Ya ;

Kong, Wangqing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (27) :10282-10291

[29] Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes [J].

Peng, Jin-Bao ;

Geng, Hui-Qing ;

Li, Da ;

Qi, Xinxin ;

Ying, Jun ;

Wu, Xiao-Feng .

ORGANIC LETTERS, 2018, 20 (16) :4988-4993

[30] Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines [J].

Ping, Yuanyuan ;

Wang, Kuai ;

Pan, Qi ;

Ding, Zhengtian ;

Zhou, Zhijun ;

Guo, Ya ;

Kong, Wangqing .

ACS CATALYSIS, 2019, 9 (08) :7335-7342

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