Enantioselective α,α-Chlorofluorination of Sulfoxonium Ylides
The first examples of enantioselective α,α-chlorofluorination of α-carbonylsulfoxonium ylides are described. Herein, two modes of reaction are explored, using chiral aminosulfoxonium ylides and a chiral fluorinating reagent, prepared <i>in situ</i> from commercially available cinchona alkaloids. Using these approaches, 25 examples of gem-dihalogenated compounds (including bromochlorination) were obtained in good yields (up to 90%) and enantioselectivity (up to 96:4 er).
Authors
- Eduardo F. Mizobuchi
- Camila Batista Pinto (ORCID: https://orcid.org/0000-0003-4490-6288)
- Marcio Hayashi (ORCID: https://orcid.org/0000-0001-8380-3068)
- Viktor Saraiva Câmara (ORCID: https://orcid.org/0000-0003-4965-0111)
- Lucas G. Furniel (ORCID: https://orcid.org/0000-0003-1280-1449)
- Radell Echemendía (ORCID: https://orcid.org/0000-0001-5310-2068)
- Javier Ellena (ORCID: https://orcid.org/0000-0002-0676-3098)
- Kauê C. Capellaro
- Leandro Wang Hantao
- Ana B. A. M. Salata
- Jackson A. L. Filho
Institutions
- Universidade Estadual de Campinas (UNICAMP) (BR)
- Institute of Physics (PL)
- Institute of Mathematics and Computer Science (MD)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c05062
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00