A Novel Approach to a-Arylacetonitrile Skeletons via para-Selective Alkylation of Protected Anilines

被引:7
作者
Deng, Zefeng [1 ]
Fan, Weitai [1 ]
Liu, Jian [1 ]
Tu, Guangliang [1 ]
Huang, Pengcheng [1 ]
Xu, Xu [1 ]
Tan, Jie [1 ]
Ji, Shun-Jun [1 ]
Zhao, Yingsheng [1 ,2 ,3 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Peoples R China
[3] Suzhou Key Lab Novel Semicond Optoelect Mat & Devi, Suzhou, Peoples R China
关键词
Aniline; & alpha; -arylacetonitrile skeletons; para-selectivity; ruthenium catalyst; C-H DIFLUOROMETHYLATION; META; ARENES; BROMINATION; NITRILES;
D O I
10.1002/chem.202300905
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A ruthenium-catalyzed para-selective alkylation of protected anilines to construct a-arylacetonitrile skeletons has been reported. We firstly disclosed the ethyl 2-bromo-2-cyanopropanoate was an effective alkylating reagent in ruthenmuim-catalyzed remote-selective C-H functionalization. A wide variety of a-arylacetonitrile skeletons can be directly obtained with moderate to good yields. Importantly, the products contain both nitrile and ester groups guaranteeing its direct transformation into other useful synthetic units, indicating the synthetic importance of this method.
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页数:5
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共 44 条
[1]  
Author A., 2021, ANGEW CHEM INT EDIT, V60, P1
[2]   Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes [J].
Deng, Guojun ;
Zhao, Liang ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6278-6282
[3]   Cyclic nitriles: tactical advantages in synthesis [J].
Fleming, FF ;
Zhang, ZY .
TETRAHEDRON, 2005, 61 (04) :747-789
[4]   Visible-Light-Enabled Ruthenium-Catalyzed meta-C-H Alkylation at Room Temperature [J].
Gandeepan, Parthasarathy ;
Koeller, Julian ;
Korvorapun, Korkit ;
Mohr, Jens ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (29) :9820-9825
[5]   Ruthenium-Catalyzed Para-Selective Oxidative Cross-Coupling of Arenes and Cycloalkanes [J].
Guo, Xiangyu ;
Li, Chao-Jun .
ORGANIC LETTERS, 2011, 13 (19) :4977-4979
[6]   meta-Selective C-H Bond Alkylation with Secondary Alkyl Halides [J].
Hofmann, Nora ;
Ackermann, Lutz .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (15) :5877-5884
[7]   Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources [J].
Hu, Di ;
Pi, Chao ;
Hu, Wei ;
Han, Xiliang ;
Wu, Yangjie ;
Cui, Xiuling .
CHINESE CHEMICAL LETTERS, 2022, 33 (08) :4064-4068
[8]   Gold-Catalyzed Hydroarylation of Alkenes with Dialkylanilines [J].
Hu, Xingbang ;
Martin, David ;
Melaimi, Mohand ;
Bertrand, Guy .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (39) :13594-13597
[9]   Novel 4,4-Disubstituted Piperidine-Based C-C Chemokine Receptor-5 Inhibitors with High Potency against Human Immunodeficiency Virus-1 and an Improved human Ether-a-go-go Related Gene (hERG) Profile [J].
Kazmierski, Wieslaw M. ;
Anderson, Don L. ;
Aquino, Christopher ;
Chauder, Brian A. ;
Duan, Maosheng ;
Ferris, Robert ;
Kenakin, Terrence ;
Koble, Cecilia S. ;
Lang, Dan G. ;
Mcintyre, Maggie S. ;
Peckham, Jennifer ;
Watson, Christian ;
Wheelan, Pat ;
Spaltenstein, Andrew ;
Wire, Mary B. ;
Svolto, Angilique ;
Youngman, Michael .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (11) :3756-3767
[10]   Synergistic Effect of a Bis(proazaphosphatrane) in Mild Palladium-Catalyzed Direct α-Arylations of Nitriles with Aryl Chlorides [J].
Kim, So Han ;
Jang, Wonseok ;
Kim, Min ;
Verkade, John G. ;
Kim, Youngjo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (27) :6025-6029