The first efficient access to -difluoromethyl amides, carbamates, thiocarbamates, ureas, formamides, and their derivatives is reported herein. The synthetic strategy relies on the initial synthesis and straightforward derivatization of -CFH carbamoyl fluorides, which were prepared through a desulfurization-fluorination of thioformamides (─NH─C(H)═S) coupled with carbonylation. The newly made -CFH carbonyl compounds proved to be highly robust and compatible with numerous chemical transformations and downstream derivatizations, underscoring the potential of this novel motif as a building block in complex functional molecules.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10913043 | PMC |
| http://dx.doi.org/10.1021/jacs.3c13711 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines.
Org Lett
January 2025
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Herein, a -phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as a metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this polymer demonstrates outstanding stability, extensive surface area, and exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency and recyclability in the photochemically driven difluoromethylation/cyclization reactions.
View Article and Find Full Text PDFCFH-synthon enables asymmetric radical difluoroalkylation for synthesis of chiral difluoromethylated amines.
Nat Commun
January 2025
Department of Pharmacy, The First Affiliated Hospital of USTC, Division of Life Sciences and Medicine, University of Science and Technology of China, Hefei, China.
The difluoromethyl group is a crucial fluorinated moiety with distinctive biological properties, and the synthesis of chiral CF₂H-containing analogs has been recognized as a powerful strategy in drug design. To date, the most established method for accessing enantioenriched difluoromethyl compounds involves the enantioselective functionalization of nucleophilic and electrophilic CF₂H synthons. However, this approach is limited by lower reactivity and reduced enantioselectivity.
View Article and Find Full Text PDFOrganic Photoredox Catalytic Difluoroalkylation of Unactivated Olefins to Access Difluoro-Containing Tetrahydropyridazines.
Org Lett
November 2024
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Herein, we disclose a readily available phenothiazine derivative as an organocatalyst, which upon excitation with 371 nm light acquires a strongly reducing power and serves to induce the radical cascade difluoromethylation/cyclization reaction of -homoallylacetohydrazides. A variety of CFCOR-tetrahydropyridazines have been obtained in moderate to excellent yields. This catalytic platform proceeds under metal-free conditions with a wide substrate scope and broad functional group compatibility, which unlocks the new reactivity of phenothiazine derivatives and adds significant synthetic value to -heterocycles.
View Article and Find Full Text PDFAccessing structurally diverse aryl difluoromethyl ethers with bromo(difluoro)acetic acid.
Chem Commun (Camb)
November 2024
Laboratory for Sustainable Catalysis and Organic Synthesis, Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy 502 285, Telangana, India.
We report a new streamlined approach for the difluoromethylation of ubiquitous phenols using inexpensive bromo(difluoro)acetic acid, yielding a wide array of structurally diverse OCFH-based building blocks in a single step. This method displays broad functional group compatibility and is amenable for effective late-stage diversification and lignin-derived monomers.
View Article and Find Full Text PDFThree-Component Photochemical Cyclization/Dithiocarbamate Formation of -Difluoro Quinolin-2(1)-ones.
Org Lett
November 2024
College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China.
Herein, a novel visible-light-induced 6- difluoromethylation cyclization and subsequent carbo-thioesterification reaction is described. This protocol allows efficient access to valuable -difluoro quinolin-2(1)-ones in moderate to excellent yields under mild conditions. Broad amino sources compatibility, including cyclic morpholine, thiazolidine, thiomorpholine, pyrrolidine, 1,4-oxazepane, 2,6-dimethylmorpholine, -butyl piperazine-1-carboxylate and noncyclic diethylamine, -ethylpropan-1-amine, -benzylethanamine, -benzyl-trimethylsilanamine, dibenzylamine, and -(4-methoxybenzyl)ethanamine, demonstrated the practicability of this strategy.
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!