Palladium-Catalyzed C8-H Acylation of 1-Naphthylamines with Acyl Chlorides

被引：46
作者：
Yu, Xiaomeng [1 ]
Yang, Fan [1 ]
Wu, Yusheng [2 ,3 ]
Wu, Yangjie [1 ]
机构：
[1] Zhengzhou Univ, Key Lab Appl Chem Henan Univ, Coll Chem & Mol Engn, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Henan, Peoples R China
[2] Tetranov Biopharm LLC, Zhengzhou 450052, Henan, Peoples R China
[3] Collaborat Innovat Ctr New Drug Res & Safety Eval, Zhengzhou 450052, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
基金：
中国国家自然科学基金;
关键词：
MERGING PHOTOREDOX CATALYSIS; DIRECTED C(SP(2))-H; 8-AMINOQUINOLINE AMIDES; C5-H PHOSPHONATION; DERIVATIVES; CYANATION; AMINATION; FUNCTIONALIZATION; ETHERIFICATION; NAPHTHYLAMIDES;
D O I：
10.1021/acs.orglett.9b00283
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile and efficient protocol for palladium-catalyzed regioselective C8-H acylation of 1-naphthylamine derivatives with acyl chlorides has been developed. The reaction exhibits broad functional group tolerance, and both aromatic and alpha,beta-unsaturated acyl chlorides can be effectively coupled with 1-naphthylamines. Moreover, the picolinamide moiety as a bidentate directing likely plays a key role in this regioselective transformation.
引用
收藏
页码：1726 / 1729
页数：4
相关论文
共 42 条
[1]   Ru/Cu Photoredox or Cu/Ag Catalyzed C4-H Sulfonylation of 1-Naphthylamides at Room Temperature [J].
Bai, Peirong ;
Sun, Suyan ;
Li, Zexian ;
Qiao, Huijie ;
Su, Xiaoxue ;
Yang, Fan ;
Wu, Yusheng ;
Wu, Yangjie .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) :12119-12127
[2]   Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids [J].
Fang, Ping ;
Li, Mingzong ;
Ge, Haibo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :11898-11899
[3]   Cobalt-Catalyzed, Aminoquinoline-Directed C(sp2)-H Bond Alkenylation by Alkynes [J].
Grigorjeva, Liene ;
Daugulis, Olafs .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) :10209-10212
[4]   Direct Cyanation of Picolinamides Using K4[Fe(CN)6] as the Cyanide Source [J].
Guan, Dinghui ;
Han, Lu ;
Wang, Lulu ;
Song, He ;
Chu, Wenyi ;
Sun, Zhizhong .
CHEMISTRY LETTERS, 2015, 44 (06) :743-745
[5]   Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives [J].
Han, Jiao-Na ;
Du, Cong ;
Zhu, Xinju ;
Wang, Zheng-Long ;
Zhu, Yue ;
Chu, Zhao-Yang ;
Niu, Jun-Long ;
Song, Mao-Ping .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :2090-2097
[6]   Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides with Alkyl Halides via Bidentate-Chelation Assistance [J].
Huang, Lehao ;
Sun, Xudong ;
Li, Qian ;
Qi, Chenze .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) :6720-6725
[7]   Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System [J].
Huang, Lehao ;
Li, Qian ;
Wang, Chen ;
Qi, Chenze .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3030-3038
[8]   Palladium-Catalyzed pen-Selective Chalcogenation of Naphthylamines with Diaryl Disulfides and Diselenides via C-H Bond Cleavage [J].
Iwasaki, Masayuki ;
Kaneshika, Wataru ;
Tsuchiya, Yuta ;
Nakajima, Kiyohiko ;
Nishihara, Yasushi .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23) :11330-11338
[9]   Direct Decarboxylative Meta-Selective Acylation of Arenes via an Ortho-Ruthenation Strategy [J].
Jing, Kun ;
Li, Zhong-Yuan ;
Wang, Guan-Wu .
ACS CATALYSIS, 2018, 8 (12) :11875-11881
[10]   Ruthenium-Catalyzed Amino- and Alkoxycarbonylations with Carbamoyl Chlorides and Alkyl Chloroformates via Aromatic C-H Bond Cleavage [J].
Kochi, Takuya ;
Urano, Seiya ;
Seki, Hajime ;
Mizushima, Eiichiro ;
Sato, Mitsuo ;
Kakiuchi, Fumitoshi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (08) :2792-+
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