Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries and different strategies have been designed for their synthesis. The last two decades witnessed the emergence of difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises the reactions of difluorocarbene generated from Ruppert-Prakash reagent (TMSCF) and its derivatives TMSCFCl and TMSCFBr. Among the various fluorination techniques available, the difluorocarbene chemistry offers a cost effective and easy procedure, opening avenue to a large number of organofluorine compounds. This review details the developments in the utility of difluorocarbene generated from TMSCF and its derivatives, till date.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/tcr.202400243 | DOI Listing |
Chem Rec
March 2025
Department of Chemistry, CMS College Kottayam (Autonomous), Kerala, 686001, India.
Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries and different strategies have been designed for their synthesis. The last two decades witnessed the emergence of difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises the reactions of difluorocarbene generated from Ruppert-Prakash reagent (TMSCF) and its derivatives TMSCFCl and TMSCFBr.
View Article and Find Full Text PDFNat Chem
February 2025
Department of Chemistry, National University of Singapore, Singapore, Singapore.
Skeletal editing of heterocyclic building blocks offers an appealing way to expand the accessible chemical space by diversifying molecular scaffolds for drug discovery. Despite the recent boom in this area, catalytic strategies that directly introduce fluorine into the backbone of small-ring heterocycles remain rare owing to the challenges of strain-induced ring cleavage and defluorination. Here we describe a copper-catalysed approach for skeletal expansion of oxygen heterocycles by reaction with a difluorocarbene species generated in situ to induce carbon atom insertion.
View Article and Find Full Text PDFChem Sci
January 2025
Department of Spine Surgery and Musculoskeletal Tumor, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University Wuhan 430071 China
Replacement of a carbonyl group with fluorinated bioisostere (, CF[double bond, length as m-dash]C) has been adopted as a key tactical strategy in drug design and development, which typically improves potency and modulates lipophilicity while maintaining biological activity. Consequently, new -difluoroalkenation reactions have undoubtedly accelerated this shift, and conceptually innovative practices would be of great benefit to medicinal chemists. Here we describe an expeditous protocol for the direct assembly of furan-substituted -difluoroalkenes PFTB-promoted cross-coupling of ene-yne-ketones and difluorocarbene.
View Article and Find Full Text PDFBeilstein J Org Chem
November 2024
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
We present a mechanochemical synthesis of difluoromethyl enol ethers. Utilizing an in situ generation of difluorocarbenes, ketones are efficiently converted to the target products under solvent-free conditions. The reactions proceed at room temperature and are complete within 90 minutes, demonstrating both efficiency and experimental simplicity.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States.
Environmentally respectful methods for generating and utilizing difluorocarbene (:CF) in the synthesis of a wide array of valuable difluoromethylated compounds are disclosed. In particular, the insertion of the CF moiety into aromatic/heteroaromatic alcohols, thiols, olefins, and alkynes under neat or aqueous micellar catalysis conditions is demonstrated. These methods yield both satisfactory results and significantly lower E-Factors compared to traditional synthetic approaches.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!