Metal-Free Oxidative C-H Amination of 8-Acylaminoquinolines and Anilides with N-Fluorobenzenesulfonimide

被引：47
作者：
Wang, Yang [1 ,2 ]
Wang, Ying [1 ,2 ]
Guo, Zhenyu [1 ,2 ]
Zhang, Qian [1 ,2 ]
Li, Dong [2 ]
机构：
[1] Hubei Univ Technol, Hubei Collaborat Innovat Ctr High Efficiency Util, Wuhan 430068, Peoples R China
[2] Hubei Univ Technol, Sch Mat & Chem Engn, Wuhan 430068, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 12期
基金：
中国国家自然科学基金;
关键词：
amination; hypervalent compounds; iodine; metal-free; n-fluorobenzenesulfonimide; PALLADIUM-CATALYZED DIAMINATION; BOND-FORMATION; PHENYLIODINE(III) BIS(TRIFLUOROACETATE); FUNCTIONAL MOLECULES; AMBIENT-TEMPERATURE; AROMATIC-COMPOUNDS; CHEMICAL-SYNTHESIS; GREEN CHEMISTRY; NITROGEN; ALKENES;
D O I：
10.1002/ajoc.201600389
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An oxidative C-H amination of 8-acylaminoquinolines and anilides with N-fluorobenzenesulfonimide (NFSI) has been developed. This process was mediated by a hypervalent iodine reagent PhI(OPiv)(2) under mild reaction conditions without any metallic catalyst or oxidant. The protocol showed good air and moisture tolerance, functional groups compatibility, and gave the highly site-selective amination products in moderate to good yields, providing a novel and facile method for synthesis of arylamine compounds.
引用
收藏
页码：1438 / 1441
页数：4
相关论文
共 50 条
[31]   Metal-Free Direct C-H Cyanation of Alkenes [J].
Wang, Xi ;
Studer, Armido .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) :11792-11796
[32]   Copper-Catalyzed Sequential C(sp2)/C(sp3)-H Amination of 2-Vinylanilines with N-Fluorobenzenesulfonimide [J].
Cao, Wen-Bin ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1771-1776
[33]   Synthesis of Imidazo[1,5-a]quinolines via Metal-Free Oxidative Amination of sp3 C-H Bonds [J].
Liu, Huanhuan ;
Wang, Xinfeng ;
Ma, Chen .
SYNTHESIS-STUTTGART, 2018, 50 (14) :2761-2767
[34]   Metal-Free Oxidative C-C Bond Formation through C-H Bond Functionalization [J].
Narayan, Rishikesh ;
Matcha, Kiran ;
Antonchick, Andrey P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) :14678-14693
[35]   Metal-Free Allylic C-H Amination of Vinylsilanes and Vinylboronates using Silicon or Boron as a Regioselectivity Switch [J].
Maloney, T. Parker ;
Berman, Janna L. ;
Michael, Forrest E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (45)
[36]   Metal-Free Stereoconvergent C-H Borylation of Enamides [J].
Wang, Tianhang ;
Wang, Zheng-Jun ;
Wang, Minyan ;
Wu, Lei ;
Fang, Xiaowu ;
Liang, Yong ;
Lv, Jiahang ;
Shi, Zhuangzhi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (44)
[37]   Advances in the Transition Metal-Free C-H Trifluoromethylation [J].
Chen, Demao ;
Jiang, Jianwen ;
Wan, Jie-Ping .
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (21) :2582-2594
[38]   Synergetic copper/TEMPO-catalysed benzylic C-H imidation with N-fluorobenzenesulfonimide at room temperature and tandem conversions with alcohols or arenes [J].
Shao, Zhong ;
Wang, Fang ;
Shi, Jingqi ;
Ma, Lifang ;
Li, Ziyuan .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13) :3298-3307
[39]   Room-Temperature C-H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N-Fluorobenzenesulfonimide as an Oxidant [J].
Shi, Cuiying ;
Miao, Qi ;
Ma, Lifang ;
Lu, Tao ;
Yang, Dong ;
Chen, Jiaming ;
Li, Ziyuan .
CHEMISTRYSELECT, 2019, 4 (20) :6043-6047
[40]   Metal-Free Oxidative C-H Amidation of N,N-Diarylureas with PhI(OAc)2: Synthesis of Benzimidazol-2-one Derivatives [J].
Yu, Jipan ;
Gao, Chang ;
Song, Zhixuan ;
Yang, Haijun ;
Fu, Hua .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (26) :5869-5875
12345