Copper-catalyzed three-component radical aminoazolation of vinylarenes with N-fluorobenzenesulfonimide and trimethylsilylazole derivatives

被引:0
作者
Yuan, Qingbing [1 ,2 ]
Wu, Caiqiong [1 ]
Bao, Yonghu [1 ]
Huang, Zengming [3 ]
Wang, Hua [1 ,2 ]
Wei, Yun [1 ]
Wang, Shaowu [3 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat,Minist Educ, Wuhu 241002, Peoples R China
[2] Anhui Zhongtian New Mat Technol Co Ltd, Wuhu 241206, Anhui, Peoples R China
[3] Anhui Polytech Univ, Coll Chem & Environm Engn, Anhui Lab Funct Complexes Mat Chem & Applicat, Wuhu 241000, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
ALKENES; STYRENES; AMINOOXYGENATION; AMINATION; ALKYNES; AZOLES; ACCESS;
D O I
10.1039/d5cc01080b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed three-component radical aminoazolation of vinylarenes with N-fluorobenzenesulfonimide (NFSI) and trimethylsilylazole derivatives has been developed. This methodology provides an efficient and straightforward approach to generate various beta-sulfoamino azoles in good to excellent yields. The protocol features exclusive chemo- and regioselectivity, and excellent functional group tolerance under mild conditions.
引用
收藏
页码:9238 / 9241
页数:4
相关论文
共 43 条
[1]   Development of Oxadiazole-Sulfonamide-Based Compounds as Potential Antibacterial Agents [J].
Ali, Asghar ;
Hasan, Phool ;
Irfan, Mohammad ;
Uddin, Amad ;
Khan, Ashba ;
Saraswat, Juhi ;
Maguire, Ronan ;
Kavanagh, Kevin ;
Patel, Rajan ;
Joshi, Mukesh C. ;
Azam, Amir ;
Mohsin, Mohd ;
Haque, Qazi Mohd Rizwanul ;
Abid, Mohammad .
ACS OMEGA, 2021, 6 (42) :27798-27813
[2]   Copper-catalyzed intermolecular aminochlorination of alkenes [J].
Arteaga, Gean C. ;
Saavedra-Olavarria, Jorge ;
Almendras, Sebastian ;
Hermosilla-Ibanez, Patricio ;
Almodovar, Iriux ;
Perez, Edwin G. .
TETRAHEDRON LETTERS, 2018, 59 (12) :1091-1093
[3]   Pd-Catalyzed and ligand-enabled alkene difunctionalization via unactivated C-H bond functionalization [J].
Barve, Balaji D. ;
Kuo, Yao-Haur ;
Li, Wen-Tai .
CHEMICAL COMMUNICATIONS, 2021, 57 (91) :12045-12057
[4]   Copper-Catalyzed Benzylic C-H Cross-Coupling Enabled by Redox Buffers: Expanding Synthetic Access to Three-Dimensional Chemical Space [J].
Chen, Si-Jie ;
Krska, Shane W. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (24) :3604-3615
[5]   Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes [J].
Coombs, John R. ;
Morken, James P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) :2636-2649
[6]   Sulfonamides: Antiviral Strategy for Neglected Tropical Disease Virus [J].
Dash, Rudra Narayan ;
Moharana, Alok Kumar ;
Subudhi, Bharat Bhusan .
CURRENT ORGANIC CHEMISTRY, 2020, 24 (09) :1018-1041
[7]  
Elke L., 2009, [No title captured], Patent No. [WO2009030715A1, 2009030715]
[8]  
Franz E., 1985, CHEM BER-RECL, V118, P3872
[9]   Asymmetric Pd(II)-Catalyzed C-O, C-N, C-C Bond Formation Using Alkenes as Substrates: Insight into Recent Enantioselective Developments [J].
Giofre, Sabrina ;
Molteni, Letizia ;
Beccalli, Egle M. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (02)
[10]   N-Fluorobenzenesulfonimide: a useful and versatile reagent for the direct fluorination and amination of (hetero)aromatic C-H bonds [J].
Gu, Qiang ;
Vessally, Esmail .
RSC ADVANCES, 2020, 10 (28) :16756-16768