Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

被引：45

作者：

Nakamura, Yuzo ^{[1
]}

Fujiu, Motohiro ^{[1
]}

Murase, Tatsuya ^{[1
]}

Itoh, Yoshimitsu ^{[1
]}

Serizawa, Hiroki ^{[1
]}

Aikawa, Kohsuke ^{[1
]}

Mikami, Koichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

基金：

日本科学技术振兴机构;

关键词：

organo-fluorine; Ruppert-Prakash reagent; trifluoromethyl; trifluoromethylation; trifluoromethyl zinc; NUCLEOPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; COPPER; PERFLUOROALKYLATION; FLUORINATION;

D O I：

10.3762/bjoc.9.277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert-Prakash reagents (CF3SiR3), are not required.

引用

页码：2404 / 2409

页数：6

共 35 条

[1] A Novel and Convenient Synthesis of Benzonitriles: Electrophilic Cyanation of Aryl and Heteroaryl Bromides [J].

Anbarasan, Pazhamalai ;

Neumann, Helfried ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4217-4222

[2] FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS [J].

BURTON, DJ ;

YANG, ZY .

TETRAHEDRON, 1992, 48 (02) :189-275

[3] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

[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] REACTIONS OF BROMOTRIFLUOROMETHANE WITH ACID-DERIVATIVES IN THE PRESENCE OF ZINC [J].

FRANCESE, C ;

TORDEUX, M ;

WAKSELMAN, C .

TETRAHEDRON LETTERS, 1988, 29 (09) :1029-1030

[6] Catalysis for fluorination and trifluoromethylation [J].

Furuya, Takeru ;

Kamlet, Adam S. ;

Ritter, Tobias .

NATURE, 2011, 473 (7348) :470-477

[7]

Hiyama T., 2000, ORGANOFLUORINE COMPO, DOI [10.1007/978-3-662-04164-2, DOI 10.1007/978-3-662-04164-2]

[8] Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter [J].

Hu, Mingyou ;

Ni, Chuanfa ;

Hu, Jinbo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (37) :15257-15260

[9] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkynes and Aryl Boronic Acids Using (Trifluoromethyl)trimethylsilane [J].

Jiang, Xueliang ;

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (03) :1251-1257

[10]

Jin Z, 2012, ALDRICHIM ACTA, V45, P67

← 1 2 3 4 →