Oxidative Povarov Reaction via sp3 C-H Oxidation of N-Benzylanilines Induced by Catalytic Radical Cation Salt: Synthesis of 2,4-Diarylquinoline Derivatives

被引:88
作者
Liu, Jing
Liu, Fang
Zhu, Yingzu
Ma, Xingge
Jia, Xiaodong [1 ]
机构
[1] Northwest Normal Univ, Minist Educ, Key Lab Ecoenvironm Related Polymer Mat, Lanzhou 730070, Gansu, Peoples R China
关键词
DIELS-ALDER REACTION; DEHYDROGENATIVE COUPLING REACTION; TERTIARY-AMINES; FACILE SYNTHESIS; BONDS; CONSTRUCTION; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.5b00244
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative Povarov reaction of N-benzylanilines was realized under catalytic radical cation salt induced conditions. The mechanism studies revealed that a radical intermediate was involved in this catalytic oxidation. This method provides a new way to synthesize 2,4-diarylquinoline derivatives.
引用
收藏
页码:1409 / 1412
页数:4
相关论文
共 30 条
[1]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[2]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[3]   A CAN-initiated aza-Diels-Alder reaction for a facile synthesis of 4-amido-N-yl tetrahydroquinolines [J].
Han, Bing ;
Jia, Xiao-Dong ;
Jin, Xiao-Ling ;
Zhou, Yu-Lu ;
Yang, Li ;
Liu, Zhong-Li ;
Yu, Wei .
TETRAHEDRON LETTERS, 2006, 47 (21) :3545-3547
[4]  
Jia XD, 2003, SYNLETT, P1707
[5]   Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives [J].
Jia, Xiao-dong ;
Ren, Yan ;
Huo, Cong-de ;
Wang, Wen-Juan ;
Chen, Xiang-Ning ;
Xu, Xiao-Lan ;
Wang, Xi-cun .
TETRAHEDRON LETTERS, 2010, 51 (51) :6779-6782
[6]   Cation radical aza-Diels-Alder reaction between N-arylimines and N-vinyllactams:: A facile synthesis of 4-lactam-N-yl tetrahydroquinolines [J].
Jia, Xiaodong ;
Han, Bing ;
Zhang, Wei ;
Jin, Xiaoling ;
Yang, Li ;
Liu, Zhong-Li .
SYNTHESIS-STUTTGART, 2006, (17) :2831-2836
[7]   Catalytic Oxidation of C(sp3)-H Bonds Induced by a Radical Cation Salt: Construction of 1,4-Dihydropyridines Using a Fragment-Reassembly Strategy [J].
Jia, Xiaodong ;
Wang, Yaxin ;
Peng, Fangfang ;
Huo, Congde ;
Yu, Liangling ;
Liu, Jing ;
Wang, Xicun .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) :1210-1216
[8]   Catalytic sp3 C-H Oxidation of Peptides and Their Analogues by Radical Cation Salts: From Glycine Amides to Quinolines [J].
Jia, Xiaodong ;
Wang, Yaxin ;
Peng, Fangfang ;
Huo, Congde ;
Yu, Liangliang ;
Liu, Jing ;
Wang, Xicun .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) :9450-9456
[9]   Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions [J].
Jia, Xiaodong ;
Peng, Fangfang ;
Qing, Chang ;
Huo, Congde ;
Wang, Yaxin ;
Wang, Xicun .
TETRAHEDRON LETTERS, 2013, 54 (36) :4950-4952
[10]   Radical cation salt induced Povarov reaction between iminoethyl glyoxylate and N-vinylamides: synthesis of quinoline-2-carboxylate derivatives [J].
Jia, Xiaodong ;
Qing, Chang ;
Huo, Congde ;
Peng, Fangfang ;
Wang, Xicun .
TETRAHEDRON LETTERS, 2012, 53 (52) :7140-7142