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Preparation of diverse -functionalized porphyrins involves iodine(III)- and copper triflate-promoted dehydrogenative coupling of -free porphyrins and appropriate NH-free heterocycles. Reaction conditions involving the stable and recyclable iodobenzene diacetate reagent are compatible with a range of NH-free heterocycles (acridone, phenoxazine and phenothiazine, carbazole, β-carbolin triazoles, imidazole, pyrazole, indazole, and tetrazole) and porphyrins to access diversely functionalized AB, ABC, and AB porphyrins in moderate to good yields. The prepared heterocycle-appended porphyrins exhibit modestly red-shifted Soret and Q bands in the absorption spectra.
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http://dx.doi.org/10.1021/acs.joc.4c02634 | DOI Listing |
Org Biomol Chem
April 2025
School of Chemical Engineering and Technology, Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300401, P. R. China.
An efficient and convenient pathway to synthesize diverse 3 or 4-oxo-alkyl substituted 1,2,4-triazine-3,5(2,4)-diones has been reported an atom- and step-economical cross-dehydrogenation coupling strategy with good functional group tolerance and wide substrate scope. The present transformation employs inexpensive manganese salt catalysts and iodobenzene diacetate oxidants at room temperature. The synthetic utility of this pathway is further demonstrated by a gram scale reaction.
View Article and Find Full Text PDFOrg Biomol Chem
March 2025
School of Chemical Sciences, National Institute of Science Education and Research (NISER)-Bhubaneswar, Jatni campus, Bhubaneswar-752050, Odisha, India.
Kynurenine metabolites are derived from the aromatic amino acid, tryptophan, and their chemical synthesis has been sought to understand the tryptophan-kynurenine-based biochemical reactions that could provide opportunities for exploring therapeutic values. This report describes the synthesis of kynurenine (kyn) derivatives from tryptophan-containing peptides using the versatile hypervalent iodine reagent, phenyliodine(III)diacetate (PIDA), through the C-C bond fragmentation of tryptophan's indole ring. However, BocNH-Trp-OH and -arylated (both benzenoid and non-benzenoid) tryptophan derivatives produce unique spirocyclic molecules with PIDA under similar reaction conditions.
View Article and Find Full Text PDFJ Inorg Biochem
June 2025
Department of Chemistry and Biochemistry, Western Kentucky University, 1906 College Heights Blvd. #11079, Bowling Green, KY 42101-1079, United States of America. Electronic address:
In this study, manganese(IV)-oxo phthalocyanines [Mn(Pc)(O)] (3) (Pc = phthalocyanine) were produced either through visible light photolysis of [Mn(Pc)(ClO)] or by chemical oxidation of [Mn(Pc)Cl] (1) with iodobenzene diacetate. The manganese(IV)-oxo species under study include tetra-tert-butylphthalocyaine‑manganese(IV)-oxo (3a) and phthalocyanine‑manganese(IV)-oxo (3b). As anticipated, the generated 3 reacted with various organic substrates to yield the oxidized products and further proved to be a competent oxidant via an HO isotope labeling experiment.
View Article and Find Full Text PDFJ Org Chem
March 2025
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India.
Preparation of diverse -functionalized porphyrins involves iodine(III)- and copper triflate-promoted dehydrogenative coupling of -free porphyrins and appropriate NH-free heterocycles. Reaction conditions involving the stable and recyclable iodobenzene diacetate reagent are compatible with a range of NH-free heterocycles (acridone, phenoxazine and phenothiazine, carbazole, β-carbolin triazoles, imidazole, pyrazole, indazole, and tetrazole) and porphyrins to access diversely functionalized AB, ABC, and AB porphyrins in moderate to good yields. The prepared heterocycle-appended porphyrins exhibit modestly red-shifted Soret and Q bands in the absorption spectra.
View Article and Find Full Text PDFJ Chromatogr A
February 2025
College of Chemistry and Materials Engineering, Bohai University, Jinzhou, Liaoning Province 121013, PR China.
Chiral synthesis of single chiral drugs offers high efficiency, controllable costs, and excellent enantioselectivity, making it crucial in the pharmaceutical industry. A significant number of studies on chiral drug synthesis primarily focuses on the design and synthesis of innovative chiral catalysts and ligands with extremely high selectivity, as well as the development of new methods and strategies. Nonetheless, the on-line monitoring of chiral drug synthesis and its underlying mechanisms remain obscure.
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