4.5 Review

State-of-the-Art in Electrophilic Trifluoromethylthiolation Reagents

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 34, Issue 5, Pages 445-454

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201500890

Keywords

fluorine; sulfur; electrophilic addition; synthetic methods

Funding

  1. CNRS
  2. Uniyersite de Rouen
  3. INSA de Rouen
  4. LABEX SynOrg [ANR-11-LABX-0029]
  5. Region Haute-Normandie
  6. Ministere de la Recherche et de l'Enseignement Superieun

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The trifluoromethylthio group (SCF3) is a fluorine chemotype that has experienced a strong acceleration of interest in the recent years. It is particularly true of the construction of new fluorinated architectures by electrophilic trifluoromethylthiolation. The spread of knowledge was already very active in this research domain in the sixties; however, gaseous and highly toxic trifluoromethanesulfenyl chloride (CF3SCl) was the only reagent available at that time. Nowadays, one really can speak of a revival in the field thanks to the rapid development of a wide panoply of reagents that are stable and easy to handle. This review provides a historical perspective of the development of shelf-stable electrophilic trifluoromethylthiolation reagents.

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