Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives

被引：93

作者：

Kondo, Hideaki ^{[1
]}

Oishi, Masahiro ^{[1
]}

Fujikawa, Kenichi ^{[1
]}

Amii, Hideki ^{[1
,2
]}

机构：

[1] Kobe Univ, Grad Sch Sci, Dept Chem, Nada Ku, Kobe, Hyogo 6578501, Japan

[2] Gunma Univ, Grad Sch Engn, Dept Chem & Chem Biol, Gunma 3768515, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 08期

基金：

日本科学技术振兴机构;

关键词：

aromatic substitution; copper; cross-coupling; retro reactions; trifluoromethylation; NUCLEOPHILIC TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; CONVENIENT METHOD; STABLE REAGENTS; ARYL HALIDES; C-C; PALLADIUM; BOND; PERFLUOROALKYL; REACTIVITY;

D O I：

10.1002/adsc.201000825

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Starting from a readily available fluoral derivative, catalytic aromatic trifluoromethylation has been successfully achieved. A small amount of copper(I) iodide-phenanthroline complex catalyzed the cross-coupling reactions of aryl/heteroaryl iodides with the O-silylated hemiaminal of fluoral (trifluoroacetaldehyde) to provide trifluoromethylated arenes in moderate to high yields.

引用

页码：1247 / 1252

页数：6

共 68 条

[1]

[Anonymous], 2004, MODERN FLUOROORGANIC

[2] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[3]

Banks R. E., 1994, ORGANOFLUORINE CHEM

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[6] New stable reagents for the nucleophilic trifluoromethylation. Part 2: Trifluoromethylation with silylated hemiaminals of trifluoroacetaldehyde [J].

Billard, T ;

Langlois, BR ;

Blond, G .

TETRAHEDRON LETTERS, 2000, 41 (45) :8777-8780

[7] New stable reagents for the nucleophilic trifluoromethylation.: 1.: Trifluoromethylation of carbonyl compounds with N-formylmorpholine derivatives [J].

Billard, T ;

Bruns, S ;

Langlois, BR .

ORGANIC LETTERS, 2000, 2 (14) :2101-2103

[8] Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].

Bouchy, A ;

Rinaldi, D ;

Rivail, JL .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281

[9] A REMARKABLY SIMPLE PREPARATION OF (TRIFLUOROMETHYL)CADMIUM AND (TRIFLUOROMETHYL) ZINC REAGENTS DIRECTLY FROM DIFLUORODIHALOMETHANES [J].

BURTON, DJ ;

WIEMERS, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (17) :5014-5015

[10] SODIUM PERFLUOROALKANE CARBOXYLATES AS SOURCES OF PERFLUOROALKYL GROUPS [J].

CARR, GE ;

CHAMBERS, RD ;

HOLMES, TF ;

PARKER, DG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (04) :921-926

← 1 2 3 4 5 6 7 →