Copper-Mediated Halotrifluoromethylation of Unactivated Alkenes

  • An, Won
  • Ha, Neul
  • Lee, Hyun Myung
  • Malpani, Yashwardhan R.
  • Lee, Duck-Hyung
  • 외 2명
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초록

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.

키워드

copper-mediated reactionhalotrifluoromethylationlate stage modificationtrifluoromethyl group (CF3)unactivated alkenesELECTROPHILIC TRIFLUOROMETHYLATING AGENTSFLUORINATED AMINO-ACIDSCATALYZED TRIFLUOROMETHYLATIONENANTIOSELECTIVE TRIFLUOROMETHYLATION3-COMPONENT OXYTRIFLUOROMETHYLATIONNUCLEOPHILIC TRIFLUOROMETHYLATIONSODIUM TRIFLUOROMETHANESULFINATEALPHA,BETA-UNSATURATED ESTERSRADICAL TRIFLUOROMETHYLATIONPERFLUOROALKYL IODIDES
제목
Copper-Mediated Halotrifluoromethylation of Unactivated Alkenes
저자
An, WonHa, NeulLee, Hyun MyungMalpani, Yashwardhan R.Lee, Duck-HyungJung, Young-SikHan, Soo Bong
DOI
10.1002/adsc.201500731
발행일
2015-12-14
유형
Article
저널명
Journal für Praktische Chemie
357
18
페이지
3949 ~ 3960