Nickel-Catalyzed Reductive Cross-Coupling of Aziridines and Allylic Chlorides

被引:12
作者
Liu, Shuai [1 ]
Wang, Sen-Lin [1 ]
Wan, Jie [1 ]
Peng, Shuang [1 ]
Zhang, Jie-Rui [1 ]
Ding, Hua-Jiao [1 ]
Zhang, Bin [1 ]
Ni, Hai-Liang [1 ]
Cao, Peng [1 ]
Hu, Ping [1 ]
Wang, Bi-Qin [1 ]
Chen, Bin [1 ]
机构
[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China
关键词
ALLYLATION; HALIDES; 2-ARYLAZIRIDINES; AMINOFLUORINATION; SUBSTITUTION; ALKENES; ACID;
D O I
10.1021/acs.orglett.3c02399
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A nickel-catalyzed reductive cross-coupling of aziridines and allylic chlorides was realized by using manganese metal as the reducing agent. This protocol afforded a convenient approach to obtain beta-allyl-substituted arylethylamines bearing various functional groups. The utility of this reaction was also demonstrated by scale-up preparation and diverse transformations, including the synthesis of Baclofen and several bioactive molecular motifs.
引用
收藏
页码:6582 / 6586
页数:5
相关论文
共 53 条
[1]   Selective Cross-Coupling of Organic Halides with Allylic Acetates [J].
Anka-Lufford, Lukiana L. ;
Prinsell, Michael R. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :9989-10000
[2]   Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].
Brenzovich, William E., Jr. ;
Benitez, Diego ;
Lackner, Aaron D. ;
Shunatona, Hunter P. ;
Tkatchouk, Ekaterina ;
Goddard, William A., III ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522
[3]   Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates [J].
Chen, Haifeng ;
Jia, Xiao ;
Yu, Yingying ;
Qian, Qun ;
Gong, Hegui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13103-13106
[4]   Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].
Cheng, Qiang ;
Tu, Hang-Fei ;
Zheng, Chao ;
Qu, Jian-Ping ;
Helmchen, Guenter ;
You, Shu-Li .
CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969
[5]   Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines with Boronic Acids [J].
Duda, Megan L. ;
Michael, Forrest E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (49) :18347-18349
[6]   Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons [J].
Estrada, Jesus G. ;
Williams, Wendy L. ;
Ting, Stephen, I ;
Doyle, Abigail G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (19) :8928-8937
[7]   Nickel/Photo-Cocatalyzed Regioselective Ring Opening of N-Tosyl Styrenyl Aziridines with Aldehydes [J].
Fan, Pei ;
Jin, Youxiang ;
Liu, Jiawei ;
Wang, Rui ;
Wang, Chuan .
ORGANIC LETTERS, 2021, 23 (19) :7364-7369
[8]   Nickel-Catalyzed Carboxylation of Aryl and Vinyl Chlorides Employing Carbon Dioxide [J].
Fujihara, Tetsuaki ;
Nogi, Keisuke ;
Xu, Tinghua ;
Terao, Jun ;
Tsuji, Yasushi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9106-9109
[9]  
Goldfogel MJ, 2020, NICKEL CATALYSIS IN ORGANIC SYNTHESIS: METHODS AND REACTIONS, P183
[10]   Enantioselective Palladium(II)-Catalyzed Oxidative Aminofluorination of Unactivated Alkenes with Et4NF.3 HF as a Fluoride Source [J].
Hou, Chuanqi ;
Chen, Pinhong ;
Liu, Guosheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (07) :2735-2739