Synthesis of Aryl Fluorides on a Solid Support and in Solution by Utilizing a Fluorinated Solvent

被引:76
作者
Doebele, Marion [1 ]
Vanderheiden, Sylvia [1 ,2 ]
Jung, Nicole [1 ,2 ]
Braese, Stefan [1 ,2 ]
机构
[1] Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] IOC ComPlat, D-76344 Eggenstein Leopoldshafen, Germany
关键词
Balz-Schiemann reaction; combinatorial chemistry; perfluorinated solvents; solid-phase synthesis; triazenes; ARENEDIAZONIUM IONS; 2,4,6-TRIMETHYLBENZENEDIAZONIUM ION; HOMOGENEOUS SOLUTION; AROMATIC FLUORIDES; DEDIAZONIATION; DECOMPOSITION; 1-ARYL-3,3-DIALKYLTRIAZENES; BENZENEDIAZONIUM; SALTS; ACIDS;
D O I
10.1002/anie.201001507
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) F for fast: The perfluorinated solvent C 6F14 is the key to a new variant of the BalzSchiemann reaction for the synthesis of fluorinated arenes. Triazenes are converted into fluoroarenes under mild con-ditions on a support and in solution (see scheme). The method is straightforward and inexpensive, and yields previously difficult-to-prepare fluoroarenes in high purity. © 2010 wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5986 / 5988
页数:3
相关论文
共 39 条
[1]  
Anbarasan P., 2010, ANGEW CHEM, V122, P2265
[2]   Efficient Synthesis of Aryl Fluorides [J].
Anbarasan, Pazhamalai ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2219-2222
[3]   SYNTHESES OF 5-FLUORO-D/L-DOPA AND [F-18] 5-FLUORO-L-DOPA [J].
ARGENTINI, M ;
WIESE, C ;
WEINREICH, R .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 68 (02) :141-144
[4]   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
[5]   THE ACID DECOMPOSITION OF 1-ARYL-3,3-DIALKYLTRIAZENES - MECHANISTIC CHANGES AS A FUNCTION OF AROMATIC-SUBSTITUTION, NUCLEOPHILE STRENGTH, AND SOLVENT [J].
BARRIO, JR ;
SATYAMURTHY, N ;
KU, H ;
PHELPS, ME .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (08) :443-444
[6]  
Brase S., 1998, ANGEW CHEM, V110, P3614
[7]  
Chu CK, 2005, B KOREAN CHEM SOC, V26, P599
[8]  
De Jeu W.H., 1980, Physical Properties of Liquid Crystalline Materials
[9]   SYNTHESIS OF AROMATIC FLUORIDES THROUGH DIAZOTIZATION IN ANHYDROUS HYDROGEN FLUORIDE [J].
FERM, RL ;
VANDERWERF, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4809-4810
[10]   Fluorination of Boronic Acids Mediated by Silver(I) Triflate [J].
Furuya, Takeru ;
Ritter, Tobias .
ORGANIC LETTERS, 2009, 11 (13) :2860-2863