Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes

Hyunseok Oh, Areum Park, Kyu Sung Jeong, Soo Bong Han, Hyuk Lee

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Many efficient catalytic methods for the introduction of trifluoromethyl group (CF 3 ) have been reported. Among them, the addition of CF 3 and other components to alkenes is well known, and many components such as azides, cyanides, amines, and halides have been inserted into alkenes with CF 3 . However, to date the double catalytic insertion of CF 3 into an alkene is unknown. Herein, we report the catalytic 1,2-bistrifluoromethylations of alkenes catalyzed by Copper (Cu). We used two CF 3 sources, namely Umemoto's reagent and (trifluoromethyl)trimethylsilane (TMSCF 3 ). Each reagent plays a unique role during this transformation; Umemoto's reagent generates CF 3 radicals, while TMSCF 3 is used to form CF 3 anions. Copper (I) bromide (CuBr) exhibited the best catalytic activity for this reaction. We believe that CuBr oxidizes the alkyl radical, which is produced by the addition of the CF 3 radical to the alkene, to the corresponding alkyl cation, which then reacts with the CF 3 anion from TMSCF 3 to produce the desired product. This reaction tolerates a diverse set of substrates bearing functional groups such as amides, esters, ethers, ketones, protected amines, tertiary amines, and phthalimides; hence this transformation is widely applicable to a wide variety of substrates. (Figure presented.).

Original languageEnglish
Pages (from-to)2136-2140
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number9
DOIs
Publication statusPublished - 2019 Apr 23

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Alkenes
Olefins
Copper
Amines
Anions
Phthalimides
Bearings (structural)
Negative ions
Ethers
Azides
Cyanides
Substrates
Ketones
Bromides
Amides
Functional groups
Cations
Catalyst activity
Esters
Positive ions

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Oh, Hyunseok ; Park, Areum ; Jeong, Kyu Sung ; Han, Soo Bong ; Lee, Hyuk. / Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes. In: Advanced Synthesis and Catalysis. 2019 ; Vol. 361, No. 9. pp. 2136-2140.
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Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes. / Oh, Hyunseok; Park, Areum; Jeong, Kyu Sung; Han, Soo Bong; Lee, Hyuk.

In: Advanced Synthesis and Catalysis, Vol. 361, No. 9, 23.04.2019, p. 2136-2140.

Research output: Contribution to journalArticle

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