Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

Hampton, Alexander S; Hodgson, David R W; McDougald, Graham; Wang, Linhua; Sandford, Graham

Abstract

Solutions of 1,3-diketones and 1,3-ketoester derivatives react with fluorine to give the corresponding 2,2-difluoro-1,3-dicarbonyl derivatives in the presence of quinuclidine. Quinuclidine reacts with fluorine in situ to generate a fluoride ion that facilitates limiting enolization processes, and an electrophilic N-F fluorinating agent that is reactive towards neutral enol species.

Citation

Hampton, A. S., Hodgson, D. R. W., McDougald, G., Wang, L., & Sandford, G. (2024). Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas. Beilstein Journal of Organic Chemistry, 20, 460-469. https://doi.org/10.3762/bjoc.20.41

• Journal Article Type: Article
• Acceptance Date: Feb 15, 2024
• Online Publication Date: Feb 28, 2024
• Publication Date: Jan 1, 2024
• Deposit Date: Feb 29, 2024
• Publicly Available Date: Feb 29, 2024
• Journal: Beilstein Journal of Organic Chemistry
• Print ISSN: 1860-5397
• Electronic ISSN: 1860-5397
• Publisher: Beilstein-Institut
• Peer Reviewed: Peer Reviewed
• Volume: 20
• Pages: 460-469
• DOI: https://doi.org/10.3762/bjoc.20.41
• Keywords: Organofluorine, Difluoromethylene, Direct Fluorination, Electrophilic Fluorination, Difluorination
• Public URL: https://durham-repository.worktribe.com/output/2290781
• PMID: 38440170