Silver-catalysed trifluoromethylation of arenes at room temperature

被引:105
作者
Seo, Sangwon [1 ]
Taylor, John B. [2 ]
Greaney, Michael F. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
基金
英国工程与自然科学研究理事会;
关键词
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; PHOTOCHEMICAL TRIFLUOROMETHYLATION; HETEROAROMATIC-COMPOUNDS; BENZOIC-ACIDS; ARYL IODIDES; TRIFLUOROMETHANESULFINATE; PERFLUOROALKYLATION; FLUORINATION;
D O I
10.1039/c3cc41829d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A variety of heteroarenes and electron rich arenes can be trifluoromethylated at room temperature with TMSCF3, catalytic silver and PhI(OAc)(2).
引用
收藏
页码:6385 / 6387
页数:3
相关论文
共 51 条
[1]   PHOTOCHEMICAL TRIFLUOROMETHYLATION OF SOME AROMATIC AND HETEROAROMATIC-COMPOUNDS WITH TRIFLUOROMETHYL BROMIDE [J].
AKIYAMA, T ;
KATO, K ;
KAJITANI, M ;
SAKAGUCHI, Y ;
NAKAMURA, J ;
HAYASHI, H ;
SUGIMORI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) :3531-3537
[2]   SILVER(I)-CATALYZED OXIDATIVE DECARBOXYLATION OF ACIDS BY PEROXYDISULFATE - ROLE OF SILVER(II) [J].
ANDERSON, JM ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1651-&
[3]   Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].
Ball, Nicholas D. ;
Gary, J. Brannon ;
Ye, Yingda ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584
[4]   Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304
[5]   Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent [J].
Dohi, Toshifumi ;
Ito, Motoki ;
Yamaoka, Nobutaka ;
Morimoto, Koji ;
Fujioka, Hiromichi ;
Kita, Yasuyuki .
TETRAHEDRON, 2009, 65 (52) :10797-10815
[6]   Practical and innate carbon-hydrogen functionalization of heterocycles [J].
Fujiwara, Yuta ;
Dixon, Janice A. ;
O'Hara, Fionn ;
Funder, Erik Daa ;
Dixon, Darryl D. ;
Rodriguez, Rodrigo A. ;
Baxter, Ryan D. ;
Herle, Bart ;
Sach, Neal ;
Collins, Michael R. ;
Ishihara, Yoshihiro ;
Baran, Phil S. .
NATURE, 2012, 492 (7427) :95-+
[7]   Catalysis for fluorination and trifluoromethylation [J].
Furuya, Takeru ;
Kamlet, Adam S. ;
Ritter, Tobias .
NATURE, 2011, 473 (7348) :470-477
[8]   FLUORINATION WITH XENON DIFLUORIDE .21. EVIDENCE FOR FREE-RADICAL INTERMEDIATES IN TRIFLUOROACETIC-ACID CATALYZED FLUORINATIONS [J].
GREGORCIC, A ;
ZUPAN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4120-4122
[9]   Ortho-Trifluoromethylation of Functionalized Aromatic Triazenes [J].
Hafner, Andreas ;
Braese, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) :3713-3715
[10]  
Harmata M., 2010, SILVER IN ORGANIC CH