Copper-Mediated Halotrifluoromethylation of Unactivated Alkenes

被引：27

作者：

An, Won ^{[1
,2
]}

Ha, Neul ^{[1
,3
]}

Lee, Hyun Myung ^{[1
,3
]}

Malpani, Yashwardhan R. ^{[1
,3
]}

Lee, Duck-Hyung ^{[2
]}

Jung, Young-Sik ^{[1
,3
]}

Han, Soo Bong ^{[1
,3
]}

机构：

[1] Korea Res Inst Chem Technol, Bio & Drug Discovery Div, Yuseong 305600, Daejeon, South Korea

[2] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[3] Univ Sci & Technol, Dept Med & Pharmaceut Chem, Yuseong 305355, Daejeon, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 18期

关键词：

copper-mediated reaction; halotrifluoromethylation; late stage modification; trifluoromethyl group (CF3); unactivated alkenes; ELECTROPHILIC TRIFLUOROMETHYLATING AGENTS; FLUORINATED AMINO-ACIDS; CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; 3-COMPONENT OXYTRIFLUOROMETHYLATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; SODIUM TRIFLUOROMETHANESULFINATE; ALPHA; BETA-UNSATURATED ESTERS; RADICAL TRIFLUOROMETHYLATION; PERFLUOROALKYL IODIDES;

D O I：

10.1002/adsc.201500731

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A copper-mediated halotrifluoromethylation of unactivated alkenes using Umemoto's reagent and copper(I) halide (CuX, X=Cl, Br, and I) was developed. The CuX species (CuI, CuBr, and CuCl) were chosen as the source for both copper and halides because of their benchtop stability, commercial availability, and relatively low cost. Simple exchange of the copper salt provided the desired simultaneous and regioselective incorporation of the halogen atom and of the CF3 group to various alkenes. This protocol offers an efficient and practical route to various beta-halotrifluoromethylated alkanes. Further modifications of the C-Br bond to C-B, C-N and C-S bonds were performed. These derivatizations show the feasibility of late- stage modifications.

引用

页码：3949 / 3960

页数：12

共 123 条

[41] REACTION OF TRIFLUOROMETHANESULFONYL CHLORIDE WITH ALKENES CATALYZED BY A RUTHENIUM(II) COMPLEX [J].

KAMIGATA, N ;

FUKUSHIMA, T ;

YOSHIDA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1559-1560

[42]

Kieltsch I., 2007, ANGEW CHEM INT EDIT, V46, P754

[43]

Kieltsch I., 2007, ANGEW CHEM, V119, P768

[44] Generation of CF3-Containing Epoxides and Aziridines by Visible-Light-Driven Trifluoromethylation of Allylic Alcohols and Amines [J].

Kim, Eunjin ;

Choi, Sungkyu ;

Kim, Heejeong ;

Cho, Eun Jin .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (20) :6209-6212

[45]

Kirsch P., 2004, MODERN FLUOROORGANIC

[46]

Koller R., 2009, ANGEW CHEM, V121, P4396

[47] Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents [J].

Koller, Raffael ;

Stanek, Kyrill ;

Stolz, Daniel ;

Aardoom, Raphael ;

Niedermann, Katrin ;

Togni, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4332-4336

[48]

Kong W., 2013, ANGEW CHEM, V125, P13324, DOI 10.1002/ange.201307377

[49] Metal-Free Aryltrifluoromethylation of Activated Alkenes [J].

Kong, Wangqing ;

Casimiro, Maria ;

Fuentes, Noelia ;

Merino, Estibaliz ;

Nevado, Cristina .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) :13086-13090

[50] Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Desulfonylation and C(sp2)-N Bond Formation of Conjugated Tosyl Amides [J].

Kong, Wangqing ;

Casimiro, Maria ;

Merino, Estibaliz ;

Nevado, Cristina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14480-14483

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