Hypervalent Iodine(III)-Catalyzed Balz-Schiemann Fluorination under Mild Conditions

被引:66
作者
Xing, Bo [1 ]
Ni, Chuanfa [1 ]
Hu, Jinbo [1 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem,Ctr Excellence Mol Sy, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
aryl fluorides; Balz-Schiemann reaction; diazonium salts; fluorination; iodine; COPPER-MEDIATED FLUORINATION; C-H FLUORINATION; NUCLEOPHILIC AROMATIC FLUORINATION; CATALYZED FLUORINATION; ARYL FLUORIDES; SANDMEYER TRIFLUOROMETHYLATION; ELECTROPHILIC FLUORINATION; VICINAL DIFLUORINATION; GEMINAL DIFLUORINATION; FUNCTIONALIZED ARYL;
D O I
10.1002/anie.201802466
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unprecedented hypervalent iodine(III) catalyzed Balz-Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25-60 degrees C), and features a wide substrate scope and good functional-group compatibility.
引用
收藏
页码:9896 / 9900
页数:5
相关论文
共 94 条
[1]   Mild Fluorination of Chloropyridines with in Situ Generated Anhydrous Tetrabutylammonium Fluoride [J].
Allen, Laura J. ;
Muhuhi, Joseck M. ;
Bland, Douglas C. ;
Merzel, Rachel ;
Sanford, Melanie S. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12) :5827-5833
[2]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[3]  
Anbarasan P., 2010, ANGEW CHEM, V122, P2265
[4]   Efficient Synthesis of Aryl Fluorides [J].
Anbarasan, Pazhamalai ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2219-2222
[5]  
[Anonymous], 2013, Angew. Chem., Int. Ed.
[6]  
[Anonymous], 2015, ANGEW CHEM
[7]   On aromatic fluoric compounds, I A new method for its representation [J].
Balz, G ;
Schiemann, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190
[8]   Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation [J].
Banik, Steven M. ;
Mennie, Katrina M. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (27) :9152-9155
[9]   Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters [J].
Banik, Steven M. ;
Medley, Jonathan William ;
Jacobsen, Eric N. .
SCIENCE, 2016, 353 (6294) :51-54
[10]   Catalytic, Diastereoselective 1,2-Difluorination of Alkenes [J].
Banik, Steven M. ;
Medley, Jonathan William ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (15) :5000-5003