We report herein the three-component radical addition reaction of SF Cl, alkene and diazo compounds for the selective formation of α-alkyl-α-SF carbonyl compounds. The three-component addition reaction proceeded through the first reaction of SF radical with the diazo compound followed by the addition of the in situ generated carbon radical to alkene. The synthetic useful α-allyl-α-SF carbonyl compounds were successfully prepared when allyl trimethylsilanes were used as the alkene substrates. Furthermore, the three-component adducts formed from SF Cl, α-diazoacetophenones and vinyl acetates were converted into pentafluorosulfanylfurans. This transformation provided a practical and efficeint method for the synthesis of pentafluorosulfanylfurans.
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http://dx.doi.org/10.1002/anie.202208860 | DOI Listing |
Molecules
January 2025
Department of NanoBiophotonics, Max Planck Institute for Multidisciplinary Sciences (MPI-NAT), Am Fassberg 11, 37077 Göttingen, Germany.
In a search for dyes photoactivatable with visible light, fluorenes with substituents at positions 2 and 7 were prepared, and their absorption and emission spectra were studied. In particular, the synthesis route to 9-diazofluorenes with 2-(N,N-dialkylamino) and N-modified 7-(4-pyridyl) substituents was established. These compounds are initially non-fluorescent, undergo photolysis with UV or blue light, and-in non-polar media-provide orange- to red-emitting products with a large separation between absorption and emission bands.
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January 2025
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
Efficient access to pyranoisoquinoline derivatives via rhodium-catalyzed double C-H functionalization of phenyl oxadiazoles and diazo compounds has been developed. Two C-C bonds and one C-O and C-N bond formation was realized by this tandem reaction, along with the formation of two heterocycles, affording diversified pyran-fused isoquinolines in moderate to good yields with broad functional group tolerance under mild reaction conditions.
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January 2025
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via visible-light-induced ortho-acyl diazo compounds, which are rapidly intercepted by the oxygen atom of an intermolecular acyl group to form a cyclic 1,3-dipole. The in situ generated highly reactive 1,3-dipole undergoes a facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.
View Article and Find Full Text PDFSci Rep
January 2025
Univ. Grenoble Alpes, CEA, CNRS, Grenoble INP, SyMMES, Grenoble, F-38000, SyMMES, France.
Pigment particles used in tattooing may exert long terms effect by releasing diffusible degradation products. In the present work, aqueous suspensions of the organic orange diazo pigment PO13 were aged by exposure to simulated sunlight at 40 °C. The morphology and the surface charge of PO13 particles were barely modified upon aging, but primary particles were released by de-agglomeration.
View Article and Find Full Text PDFOrg Lett
January 2025
College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.
Exploration of the cascade reactivity of diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose a light-mediated de novo synthesis of esterified heterocycles under mild conditions. The reaction displays a broad functional group tolerance, including a wide variety of alkenes, diazo compounds, and some bioactive molecules.
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