4.8 Article

Direct Trifluoromethylthiolation of Aziridines: Cation-Controlled Diverse Synthesis of Trifluoromethylthiolated Isothiocyanates and Amines

Journal

ORGANIC LETTERS
Volume 24, Issue 10, Pages 2035-2039

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00558

Keywords

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Funding

  1. National Key Research and Development Program of China [2021YFF0701700]
  2. NFSC [21925105, 92156001]
  3. Natural Science Foundation of Tianjin [18JCJQJC47000]
  4. NCC Fund [NCC2020FH07]
  5. Haihe Laboratory of Sustainable Chemical Transformations
  6. Fundamental Research Funds for the Central Universities

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The direct trifluoromethylthiolation of aziridines with AgSCF3 and iodides is reported. The beta-trifluoromethylthiolated isothiocyanates and amines were selectively obtained by changing the cation of iodide. This strategy shows good tolerance to a wide range of functional groups with high yields and regioselectivities. Moreover, the obtained isothiocyanates can be used for further synthetic manipulations.
The direct trifluoromethylthiolation of aziridines with AgSCF3 and iodides is reported. The beta-trifluoromethylthiolated isothiocyanates and amines were selectively obtained by the changed cation of iodide. This strategy is tolerant to a wide range of functional groups with good yields and regioselectivities. In addition, the isothiocyanates can be used for further synthetic manipulation, which offered a convenient approach for SCF3-containing compounds.

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