We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of -difluorocyclopropanes with enamides, which provides a convenient and efficient strategy for the synthesis of multisubstituted -H pyrrole derivatives. This transformation selectively cleaves the C-C bond, two C-F bonds, and the C-N bond in a one-pot procedure. Additionally, this protocol allows for the modification of several bioactive molecules.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00241 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Modular Synthesis of Monofluorinated 1,2,4-Triazoles/1,3,5-Triazines via Defluorinative Annulations of -CF Imidoyl Chlorides.
Org Lett
March 2025
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, College of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun, 130024, China.
Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles have hardly been explored. This work reported a novel and modular synthesis of monofluorinated 1,2,4-triazoles and 1,3,5-triazines, which utilizes -CF imidoyl chlorides as unique polyfluoro synthons and their defluorinative annulations with hydrazines/imidazines.
View Article and Find Full Text PDFPd-IPent-Catalyzed Defluorinative Annulation of -Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted -H Pyrroles.
Org Lett
March 2025
Key Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing 100872, People's Republic of China.
We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of -difluorocyclopropanes with enamides, which provides a convenient and efficient strategy for the synthesis of multisubstituted -H pyrrole derivatives. This transformation selectively cleaves the C-C bond, two C-F bonds, and the C-N bond in a one-pot procedure. Additionally, this protocol allows for the modification of several bioactive molecules.
View Article and Find Full Text PDFMild [3 + 3] Annulation of (Trifluoromethyl)alkenes with Thioureas Enabled by Chemoselective Defluorinative Amination: Synthesis of 6-Fluoro-3,4-dihydropyrimidine-2(1)-thiones.
J Org Chem
January 2025
School of Chemistry and Chemical Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China.
The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1)-thiones in high yields, features transition-metal free, mild conditions, efficient, is operationally simple and gram-scalable, tolerates diverse useful functional groups.
View Article and Find Full Text PDFConstruction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF-Alkenes.
Org Lett
January 2025
Medicinal & Process Chemistry Division, Council of Scientific and Industrial Research (CSIR)-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Post Office Box 173, Lucknow 226031, India.
A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving -phenyl-α-fluoro-α-phenylsulfonylacetamide and 2-CF-alkenes to access -phenyl-3,6-difluoropyridone derivatives has been achieved. The key to the success of this single-step synthesis of difluoropyridones is the strategic utilization of 2-CF-alkenes for consecutive allylic and vinylic substitution reactions and a desulfonylation cascade. We could also show that these difluoropyridones serve as a versatile platform for C-6-selective defluorinative functionalizations.
View Article and Find Full Text PDFSynthesis of fluorine-containing bicyclo[4.1.1]octenes photocatalyzed defluorinative (4 + 3) annulation of bicyclo[1.1.0]butanes with -difluoroalkenes.
Chem Sci
January 2025
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University Xi'an 710049 China
Although bicyclo[4.1.1] systems are privileged scaffolds in many natural products and drug molecules, efficient synthetic approaches to these systems remain underdeveloped.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!