A New Method for Aromatic Difluoromethylation: Copper-Catalyzed Cross-Coupling and Decarboxylation Sequence from Aryl Iodides

被引：285

作者：

Fujikawa, Kenichi ^{[1
]}

Fujioka, Yasutaka ^{[1
]}

Kobayashi, Akira ^{[2
]}

Amii, Hideki ^{[1
,2
]}

机构：

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

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 20期

关键词：

MEDIATED FLUOROALKYLATION REACTIONS; OXIDATIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; BOND-FORMATION; PALLADIUM; ACIDS; BROMODIFLUOROACETATE; FLUORINATION; REACTIVITY; INHIBITORS;

D O I：

10.1021/ol202289z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new methodology for aromatic difluoromethylation is described. Aryl iodides reacted with alpha-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldifluoroacetates in moderate to good yields. The subsequent hydrolysis of aryldifluoroacetates and KF-promoted decarboxylation afforded a variety of difluoromethyl aromatics.

引用

页码：5560 / 5563

页数：4

共 74 条

[31]

Hope HR, 2000, J LIPID RES, V41, P1604

[32] Selective difluoromethylation and monofluoromethylation reactions [J].

Hu, Jinbo ;

Zhang, Wei ;

Wang, Fei .

CHEMICAL COMMUNICATIONS, 2009, (48) :7465-7478

[33] Cu-Mediated Chemoselective Trifluoromethylation of Benzyl Bromides Using Shelf-Stable Electrophilic Trifluoromethylating Reagents [J].

Kawai, Hiroyuki ;

Furukawa, Tatsuya ;

Nomura, Yoshinori ;

Tokunaga, Etsuko ;

Shibata, Norio .

ORGANIC LETTERS, 2011, 13 (14) :3596-3599

[34]

Kieltsch I., 2010, J FLUORINE CHEM, V131, P1108

[35]

Kim Y. S., 1963, J KOREAN CHEM, V7, P189

[36] Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide [J].

Kino, Tatsuhito ;

Nagase, Yu ;

Ohtsuka, Yuhki ;

Yamamoto, Kyoko ;

Uraguchi, Daisuke ;

Tokuhisa, Kenji ;

Yamakawa, Tetsu .

JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (01) :98-105

[37]

Kirsch P., 2013, Modern Fluoroorganic Chemistry

[38] (METHYL DIFLUOROACETATE)COPPER REAGENT - REMARKABLE SOLVENT EFFECT ON THE F-19-NMR SPECTRUM, STABILITY AND REACTIVITY [J].

KITAGAWA, O ;

TAGUCHI, T ;

KOBAYASHI, Y .

CHEMISTRY LETTERS, 1989, (03) :389-392

[39] Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate [J].

Knauber, Thomas ;

Arikan, Fatih ;

Roeschenthaler, Gerd-Volker ;

Goossen, Lukas J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (09) :2689-2697

[40] Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives [J].

Kondo, Hideaki ;

Oishi, Masahiro ;

Fujikawa, Kenichi ;

Amii, Hideki .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1247-1252

← 1 2 3 4 5 6 7 8 →