Nickel-Catalyzed Regioselective Hydroarylation of Internal Enamides

被引：20

作者：

Wang, Chenchen ^{[1
,2
]}

Xi, Yang ^{[1
,2
]}

Huang, Wenyi ^{[1
,2
]}

Qu, Jingping ^{[1
,2
]}

Chen, Yifeng ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Key Lab Adv Mat,Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Joint Int Res Lab Precis Chem & Mol Engn,Sch Chem, Shanghai 200237, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 23期

基金：

中国国家自然科学基金;

关键词：

DIRECT ARYLATION; CYCLIC ENAMIDES; ALKENES; FUNCTIONALIZATION; HYDROALKYNYLATION; HYDROAMINATION; DERIVATIVES; CYCLIZATION; MECHANISM; IRIDIUM;

D O I：

10.1021/acs.orglett.0c03542

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we disclose a nickel-catalyzed three-component reaction of internal enamide, diethoxymethylsilane, and aryl iodide to provide expedient access to benzylic amide derivatives. The protocol features a broad substrate scope with a moderate to excellent isolated yield under the mild condition. The high regioselectivity of Ni-catalyzed enamide hydroarylation can be attributed to the directing effect by the prefunctionalized nitrogen-containing group on the alkenes.

引用

页码：9319 / 9324

页数：6

共 86 条

[1] Rhodium-Catalyzed Regiodivergent and Enantioselective Hydroboration of Enamides [J].

Bai, Xiao-Yan ;

Zhao, Wei ;

Sun, Xin ;

Li, Bi-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (50) :19870-19878

[2] Highly Enantioselective Synthesis of Propargyl Amides through Rh-Catalyzed Asymmetric Hydroalkynylation of Enamides: Scope, Mechanism, and Origin of Selectivity [J].

Bai, Xiao-Yan ;

Zhang, Wen-Wen ;

Li, Qian ;

Li, Bi-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) :506-514

[3] Iridium-Catalyzed Enantioselective Hydroalkynylation of Enamides for the Synthesis of Homopropargyl Amides [J].

Bai, Xiao-Yan ;

Wang, Zi-Xuan ;

Li, Bi-Jie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) :9007-9011

[4] Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters [J].

Bera, Srikrishna ;

Hu, Xile .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (39) :13854-13859

[5] Nickel/NHC-Catalyzed Asymmetric C-H Alkylation of Fluoroarenes with Alkenes: Synthesis of Enantioenriched Fluorotetralins [J].

Cai, Yuan ;

Ye, Xiaodong ;

Liu, Sheng ;

Shi, Shi-Liang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (38) :13433-13437

[6] Enamides: valuable organic substrates [J].

Carbery, David R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460

[7] NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes [J].

Chen, Fenglin ;

Xu, Xianfeng ;

He, Yuli ;

Huang, Genping ;

Zhu, Shaolin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) :5398-5402

[8] Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters [J].

Chen, Lili ;

Zou, Xiaoliang ;

Zhao, Haonan ;

Xu, Senmiao .

ORGANIC LETTERS, 2017, 19 (13) :3676-3679

[9] Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes [J].

Chen, Yue-Gang ;

Shuai, Bin ;

Xu, Xue-Tao ;

Li, Yi-Qian ;

Yang, Qi-Liang ;

Qiu, Hui ;

Zhang, Kun ;

Fang, Ping ;

Mei, Tian-Sheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) :3395-3399

[10] Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes [J].

Derosa, Joseph ;

Apolinar, Omar ;

Kang, Taeho ;

Tran, Van T. ;

Engle, Keary M. .

CHEMICAL SCIENCE, 2020, 11 (17) :4287-4296

← 1 2 3 4 5 6 7 8 9 →