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An efficient transition-metal-free fluorination synthesis of -H-free 3-heteroaryl-oxindoles with Selectfluor was depicted. Under mild reaction conditions, a series of 3-heteroaryl-fluorooxindoles were produced in yield of 62-88% using Selectfluor as a fluorine source.
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http://dx.doi.org/10.1021/acs.joc.3c02063 | DOI Listing |
J Org Chem
August 2025
Department of Applied Chemistry, Anhui Agricultural University, 230036 Hefei, China.
We presented a Selectfluor-mediated direct oxidative -arylation of -acyl sulfenamides with naphthols via an oxidation to sulfinimidoyl fluoride/nucleophilic substitution cascade process. Notably, this methodology is time-efficient, operationally safe, and easily scalable without requiring prefunctionalized arenes or transition-metal catalysts. It exhibits excellent functional-group compatibility, providing a series of sulfilimines in good to high yields (40 examples, up to 95%).
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
School of Pharmacy, Xinxiang University, Xinxiang, Henan 453000, P. R. of China.
The three-component reaction offers a convenient method for synthesizing difluorinated compounds. In this review, we classify and discuss synthetic methodologies developed over the past decade (2014-2024) into three categories: (a) radical reactions, (b) difluorocarbene-mediated fluorination, and (c) other reaction types, including those using nucleophilic and electrophilic fluorine reagents. Various reagents such as AgF, pyridine·9HF, Selectfluor II, TMSCF, TMSCFBr, TMSCFPO(OEt), RCF, (CFCO)O, ClCFH, ClCFCONa, CFHSONa, [PhPCFH]Br, ClCFCl, BrCFR, ICFCOAr, and BrCFCOEt will be discussed.
View Article and Find Full Text PDFRSC Adv
June 2025
Organic Chemistry Group, School of Pharmacy, Naval Medical University No. 325 Guo-he Road Shanghai 200433 P. R. China
A carbamothioate-mediated method for synthesizing benzenesulfonyl fluorides Selectfluor™ oxidation is reported, enabling compatibility with α,β-unsaturated chalcone derivatives without Michael addition side reactions. This approach offers moderate yields, broad functional group tolerance, and applications in covalent drug discovery, facilitating the incorporation of sulfonyl fluoride warheads into complex electrophilic scaffolds.
View Article and Find Full Text PDFOrganic Synth
February 2025
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Checked by Sergio Armentia Matheu, Saad Shaaban, and Nuno Maulide.
View Article and Find Full Text PDFChem Rec
April 2025
Department of Chemistry, Jadavpur University, 188, Raja Subodh Chandra Mallick Rd, Jadavpur, Kolkata, West Bengal, 700032, India.
Selectfluor, [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)], is a highly valuable reagent in contemporary chemistry, serving not only as an electrophilic fluorinating agent but also as an effective catalyst in the synthesis of various pharmaceutically relevant heterocycles.
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