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
[1]   Tunable, Chemo- and Site-Selective Nitrene Transfer Reactions through the Rational Design of Silver(I) Catalysts [J].
Alderson, Juliet M. ;
Corbin, Joshua R. ;
Schomaker, Jennifer M. .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) :2147-2158
[2]   Iron-Catalyzed Intramolecular Aminations of C(sp3)-H Bonds in Alkylaryl Azides [J].
Alt, Isabel T. ;
Guttroff, Claudia ;
Plietker, Bernd .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) :10582-10586
[3]   Catalytic Synthesis of N-Heterocycles via Direct C(sp3)-H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand [J].
Bagh, Bidraha ;
Broere, Daniel L. J. ;
Sinha, Vivek ;
Kuijpers, Petrus F. ;
van Leest, Nicolaas P. ;
de Bruin, Bas ;
Demeshko, Serhiy ;
Siegler, Maxime A. ;
van der Vlugt, Jan Ivar .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (14) :5117-5124
[4]   Elusive Terminal Copper Arylnitrene Intermediates [J].
Bakhoda, Abolghasem ;
Jiang, Quan ;
Bertke, Jeffery A. ;
Cundari, Thomas R. ;
Warren, Timothy H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (23) :6426-6430
[5]   THE FE-II-FE-IV AND FE-III-FE-V MANIFOLDS IN AN EXPANDED WORLD OF GIF CHEMISTRY [J].
BARDIN, C ;
BARTON, DHR ;
HU, B ;
ROJASWAHL, R ;
TAYLOR, DK .
TETRAHEDRON LETTERS, 1994, 35 (32) :5805-5808
[6]   The importance of pyridine complexation on selective oxidation within the Fe(III)-Fe(V) manifold in Gif chemistry. [J].
Barton, DHR ;
Hu, B ;
Li, TS ;
MacKinnon, J .
TETRAHEDRON LETTERS, 1996, 37 (46) :8329-8332
[7]   Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C-H Bond Functionalization [J].
Becker, Peter ;
Duhamel, Thomas ;
Martinez, Claudio ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) :5166-5170
[8]   Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3-H Bonds [J].
Becker, Peter ;
Duhamel, Thomas ;
Stein, Christopher J. ;
Reiher, Markus ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :8004-8008
[9]   An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C-H Animation [J].
Berges, Julien ;
Garcia, Belen ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (48) :15891-15895
[10]   Iron-Catalyzed Direct C(sp3)-H Amination Reactions of Isochroman Derivatives with Primary Arylamines under Mild Conditions [J].
Chen, Di ;
Pan, Fuyou ;
Gao, Jianrong ;
Yang, Jianguo .
SYNLETT, 2013, 24 (16) :2085-2088