4.8 Article

Silver-Catalyzed Trifluoromethoxylation of Aziridines

Journal

ORGANIC LETTERS
Volume 24, Issue 3, Pages 881-885

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04226

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. Fundamental Research Funds for the Central Universities

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A silver-catalyzed trifluoromethoxylation reaction has been disclosed, enabling the synthesis of β-trifluoromethoxylated amine compounds. This method offers mild conditions, simple operations, and high selectivity for the construction of quaternary centers.
We disclose a silver-catalyzed trifluoromethoxylation of N-tosyl aziridines with trifluoromethyl arylsulfonate. The protocol is characterized by its mild conditions, simple operations, and good chemo- and regioselectivity. In addition, the trifluoromethoxylation of trisubstituted aziridines could construct C-OCF3 quaternary centers exclusively, which is quite rare. This method unlocks a new catalytic blueprint for accessing beta-trifluoromethoxylated amines, which could be important building blocks in synthetic chemistry.

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