4.8 Article

Squaramide/Li+-Catalyzed Direct SN1-Type Reaction of Vinyl Triflates with Difluoroenoxysilanes through Vinyl Cations

Journal

ORGANIC LETTERS
Volume 24, Issue 38, Pages 6978-6982

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02793

Keywords

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Funding

  1. China Scholarship Council (CSC)
  2. CNRS
  3. MESRI
  4. Universite Paris-Saclay [ANR-21-CE07-0027]
  5. Ecole Polytechnique
  6. [ANR-18-CE07-0033-01]
  7. Agence Nationale de la Recherche (ANR) [ANR-21-CE07-0027] Funding Source: Agence Nationale de la Recherche (ANR)

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Difluoromethylene-skipped enones can be readily synthesized from arylvinyltriflates and aryldifluoroenoxysilanes using a squaramide/Li+ catalyst. This strategy enables the reaction between a typically weak electrophile and a weak nucleophile, which is difficult to achieve with classical aldol/dehydration methods.
Difluoromethylene-skipped enones have been readily obtained from arylvinyltriflates and aryldifluoroenoxysilanes. While these useful compounds are difficult to synthesize by the classical aldol/dehydration approach, the use of a squaramide/Li+ catalyst allows their direct formation via a vinyl carbocation paired with a weakly coordinating perfluorinated alkoxyaluminate. This strategy makes possible a reaction between a typically weak electrophile and a weak nucleophile. Control experiments and DFT computations shed light on the mechanism of this transformation.

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