Work

Enantioselective α,α-Chlorofluorination of Sulfoxonium Ylides

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 in situ 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).

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c05062

Authors: Lucas G. Furniel, Kauê C. Capellaro, Viktor S. Câmara, Marcio Hayashi, Radell Echemendía, Camila B. Pinto, Ana B. A. M. Salata, Jackson A. L. Filho, Leandro W. Hantao, Javier Ellena, Antonio C. B. Burtoloso

Institutions: Universidade de São Paulo, Instituto de Química de São Carlos, Instituto de Física de São Carlos, Universidade Estadual de Campinas (UNICAMP)

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico

Awards: G22113365, G2470191573, G2823776494, G3261226975, G3690646728, G4539897318, G4660339451, G5088501285, G526143188, New methodologies to form C-C bonds from sulfoxonium ylides, G6191138830, G6598016484, G8717273724

OpenAlex ID: W7125960428

FWCI: 6.058

Cites: 44

Cited by: 2

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