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

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