Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide

被引：189

作者：

Kino, Tatsuhito ^{[1
,2
]}

Nagase, Yu ^{[2
]}

Ohtsuka, Yuhki ^{[1
]}

Yamamoto, Kyoko ^{[1
]}

Uraguchi, Daisuke ^{[1
]}

Tokuhisa, Kenji ^{[3
]}

Yamakawa, Tetsu ^{[1
]}

机构：

[1] Sagami Chem Res Ctr, Kanagawa 2521193, Japan

[2] Tokai Univ, Fac Engn, Dept Appl Chem, Hiratsuka, Kanagawa 2591292, Japan

[3] Tosoh F Tech Inc, Yamaguchi 7460006, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2010年 / 131卷 / 01期

关键词：

Trifluoromethylation; Trifluoromethyl iodide; Trifluoromethyl radical; PHOTOCHEMICAL TRIFLUOROMETHYLATION; RADICAL TRIFLUOROMETHYLATION; SULFUR-DIOXIDE; XENON DIFLUORIDE; TITANIUM ATE; PERFLUOROALKYLATION; TRIFLUOROIODOMETHANE; SUBSTITUTION; CHEMISTRY; TRIFLUOROMETHANESULFINATE;

D O I：

10.1016/j.jfluchem.2009.09.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：98 / 105

页数：8

共 49 条

[1] Achgill R K, 1991, US Patent, Patent No. 4987233
[2] PHOTOCHEMICAL TRIFLUOROMETHYLATION OF SOME AROMATIC AND HETEROAROMATIC-COMPOUNDS WITH TRIFLUOROMETHYL BROMIDE
AKIYAMA, T
KATO, K
KAJITANI, M
SAKAGUCHI, Y
NAKAMURA, J
HAYASHI, H
SUGIMORI, A
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) : 3531 - 3537
[3] SYNTHESIS OF PERFLUOROALKYLPYRROLES BY HOMOLYTIC SUBSTITUTION WITH PERFLUOROALKYL RADICALS
BACIOCCHI, E
MURAGLIA, E
[J]. TETRAHEDRON LETTERS, 1993, 34 (23) : 3799 - 3800
[4] HOMOLYTIC AROMATIC SUBSTITUTIONS OF PENTATOMIC HETEROAROMATICS WITH ELECTROPHILIC CARBON RADICALS GENERATED BY ALKYL-HALIDES AND TRIETHYLBORANE
BACIOCCHI, E
MURAGLIA, E
[J]. TETRAHEDRON LETTERS, 1993, 34 (31) : 5015 - 5018
[5] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[6] REACTIONS OF TRIFLUOROMETHYL RADICALS .1. PHOTOCHEMICAL REACTIONS OF TRIFLUOROIODOMETHANE WITH BENZENE AND SOME HALOGENOBENZENES
BIRCHALL, JM
IRVIN, GP
BOYSON, RA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (05): : 435 - 439
[7] New methods of free-radical perfluoroalkylation of aromatics and alkenes. Absolute rate constants and partial rate factors for the homolytic aromatic substitution by n-perfluorobutyl radical
Bravo, A
Bjorsvik, HR
Fontana, F
Liguori, L
Mele, A
Minisci, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7128 - 7136
[8] FLUOROALKYLATION OF AROMATIC-COMPOUNDS
COWELL, AB
TAMBORSKI, C
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1981, 17 (04) : 345 - 356
[9] Trifluoromethylation of aromatic compounds via Kolbe electrolysis in pure organic solvent.: Study on laboratory and pilot scale
Depecker, C
Marzouk, H
Trevin, S
Devynck, J
[J]. NEW JOURNAL OF CHEMISTRY, 1999, 23 (07) : 739 - 742
[10] Structure, reactivity, and chemistry of fluoroalkyl radicals
Dolbier, WR
[J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1557 - 1584

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