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- Title
Copper-Mediated Halotrifluoromethylation of Unactivated Alkenes.
- Authors
An, Won; Ha, Neul; Lee, Hyun Myung; Malpani, Yashwardhan R.; Lee, Duck ‐ Hyung; Jung, Young ‐ Sik; Han, Soo Bong
- Abstract
A copper-mediated halotrifluoromethylation of unactivated alkenes using UmemotoÏs 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 -β-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.
- Subjects
TRIFLUOROMETHYL compounds synthesis; COPPER compounds; REGIOSELECTIVITY (Chemistry); DERIVATIZATION; REDUCTIVE elimination (Chemistry)
- Publication
Advanced Synthesis & Catalysis, 2015, Vol 357, Issue 18, p3949
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201500731