Ligand-free iron-catalyzed benzylic C (sp3)-H amination of methylarenes with N-fluorobenzenesulfonimide

被引:13
作者
Bao, Fengyu [1 ]
Cao, Yuanbo [1 ]
Liu, Wenbo [1 ]
Zhu, Junhao [1 ]
机构
[1] Henan Agr Univ, Coll Sci, Zhengzhou 450002, Henan, Peoples R China
关键词
H BOND AMINATION; METAL-ORGANIC FRAMEWORKS; INTERMOLECULAR AMIDATION; C(SP(3))-H BONDS; 8-METHYLQUINOLINES; FUNCTIONALIZATION; OXIDATION; DESIGN; DERIVATIVES; MECHANISM;
D O I
10.1039/c9ra05294a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct conversion of cheap methylarenes to benzylic amines, which are essential structural units of important drugs, is of great significance. However, the known methodologies suffer from the requirement of noble metal catalysts, heavy metal residues or strong oxidants. Herein, the first biocompatible iron-catalyzed benzylic C (sp(3))-H amination of methylarenes with N-fluorobenzenesulfonimide is described. The reactions of methylarenes bearing electron-donating groups and electron-withdrawing groups ran smoothly under ligand and additional oxidant free conditions. Both toluene derivatives and 8-methylquinoline can be aminated by the same iron catalyst.
引用
收藏
页码:27892 / 27895
页数:4
相关论文
共 67 条
[31]   Ru(II)-catalyzed amidation reactions of 8-methylquinolines with azides via C(sp3)-H activation [J].
Liu, Bingxian ;
Li, Bin ;
Wang, Baiquan .
CHEMICAL COMMUNICATIONS, 2015, 51 (91) :16334-16337
[32]   Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions [J].
Liu, Wenbo ;
Liu, Chenjiang ;
Zhang, Yonghong ;
Sun, Yadong ;
Abdukadera, Ablimit ;
Wang, Bin ;
Li, He ;
Ma, Xuecheng ;
Zhang, Zengpeng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (26) :7154-7158
[33]   Nonheme Iron-Mediated Amination of C(sp3)-H Bonds. Quinquepyridine-Supported Iron-Imide/Nitrene Intermediates by Experimental Studies and DFT Calculations [J].
Liu, Yungen ;
Guan, Xiangguo ;
Wong, Ella Lai-Ming ;
Liu, Peng ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) :7194-7204
[35]   Asymmetric Photocatalytic C-H Functionalization of Toluene and Derivatives [J].
Mazzarella, Daniele ;
Crisenza, Giacomo E. M. ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (27) :8439-8443
[36]   MECHANISM OF THE GIF-BARTON TYPE ALKANE FUNCTIONALIZATION BY HALIDE AND PSEUDOHALIDE IONS [J].
MINISCI, F ;
FONTANA, F .
TETRAHEDRON LETTERS, 1994, 35 (09) :1427-1430
[37]   NEW FREE-RADICAL SYNTHESES UNDER GIF-BARTON OXIDATION CONDITIONS [J].
MINISCI, F ;
FONTANA, F ;
ARANEO, S ;
RECUPERO, F .
TETRAHEDRON LETTERS, 1994, 35 (22) :3759-3762
[38]   Highly Regioselective Copper-Catalyzed Benzylic C?H Amination by N-Fluorobenzenesulfonimide [J].
Ni, Zhikun ;
Zhang, Qian ;
Xiong, Tao ;
Zheng, Yiying ;
Li, Yan ;
Zhang, Hongwei ;
Zhang, Jingping ;
Liu, Qun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (05) :1244-1247
[39]   Visible-Light-Catalyzed Direct Benzylic C(sp3)-H Amination Reaction by Cross-Dehydrogenative Coupling [J].
Pandey, Ganesh ;
Laha, Ramkrishna .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) :14875-14879
[40]  
Paradine SM, 2015, NAT CHEM, V7, P987, DOI [10.1038/NCHEM.2366, 10.1038/nchem.2366]