4.3 Article

Heptafluoroisopropylthiolation of benzyl halides

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 255, Issue -, Pages -

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2022.109966

Keywords

heptafluoroisopropylthiolation; benzyl halides; hexafluoropropylene

Funding

  1. National Key Research and Development Program of China [2021YFF0701700]
  2. National Natural Science Foundation [21971252, 21991122]
  3. Program for Scientific Research Innovation Team in Colleges and Universities of Shandong Province, Jinan Science and Technology Bureau [2019GXRC021]
  4. Key Research Program of Frontier Sciences, and Chinese Academy of Sciences (CAS) [QYZDJSSWSLH049]
  5. NINGBO ZHENGGUANG RESIN., LTD

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A protocol is described for the heptafluoroisopropylthiolation of benzyl halides using a HFP/CsF/S-8 system, enabling the rapid synthesis of (CF3)2CFS-containing compounds. This method shows potential for the synthesis of biologically active molecules.
Heptafluoroisopropylthio group (-SCF(CF3)(2)) has bioactivities in insecticidal molecules, but the protocol for direct introduction of-SCF(CF3)(2) is under-explored. Described here is a protocol on heptafluoroisopropylthiolation of benzyl halides with a hexafluoropropylene (HFP)/CsF/S-8 system. The reaction enables the rapid construction of a range of (CF3)(2)CFS-containing compounds from readily available materials. This protocol may find application in the synthesis of (CF3)(2)CFS-containing biologically active molecules.

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