The in situ generated μ-oxo-bridged reactive hypervalent iodine(iii) species 1 or their analogues are introduced as more efficient organocatalysts for the catalytic strategy for realizing practical and greener oxidations.
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Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts.
Beilstein J Org Chem
December 2024
LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA FCT , 2829-516 Caparica, Portugal.
The reactivity of our recently disclosed hypervalent iodine reagents (HIRs) bearing a benzylamine with in situ-generated sulfenate salts was investigated. Under the studied conditions sulfonamides have been obtained in up to 52% yield. This reaction has been extended to a variety of HIRs and sulfenate salts to explore the different reactivity of these new reagents.
View Article and Find Full Text PDFBiocatalytic Generation of Trifluoromethyl Radicals by Nonheme Iron Enzymes for Enantioselective Alkene Difunctionalization.
J Am Chem Soc
December 2024
Department of Chemistry, Johns Hopkins University; Baltimore, Maryland 21218, United States.
The trifluoromethyl (-CF) group represents a highly prevalent functionality in pharmaceuticals. Over the past few decades, significant advances have been made in the development of synthetic methods for trifluoromethylation. In contrast, there are currently no metalloenzymes known to catalyze the formation of C(sp)-CF bonds.
View Article and Find Full Text PDFStructure and thermal stability of phosphorus-iodonium ylids.
Beilstein J Org Chem
November 2024
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Hypervalent iodine(III) reagents have become indispensable tools in organic synthesis, but gaps remain in the functionalities they can transfer. In this study, a fundamental understanding of the thermal stability of phosphorus-iodonium ylids is obtained through X-ray diffraction, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Insights into the structural factors affecting thermal stability and potential decomposition pathways will enable the future design and development of new reagents.
View Article and Find Full Text PDFNitrogenation of Alkynes with Nitrones to Prepare Functionalized [1,4]Oxazinones through Csp-Csp Bond Cleavage.
Org Lett
November 2024
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Herein, we report a novel strategy of hypervalent iodine(III) compound-mediated selective C-C bond cleavage of alkynes and C═N/N-O bond cleavage of nitrones and recombination of C-C/C-O/C-N multiple bonds to access various functionalized [1,4]oxazinones bearing a vicinal carbon stereocenter in good yields and high diastereoselectivity. Mechanistic studies revealed that the reaction undergoes a domino [4 + 3] cycloaddition, 1,3-rearrangement of N-O bond, intramolecular cyclization, dearomatization, and rearomatization over four steps in a single flask. The present method features good functional group tolerance, broad substrate scope, and C-C/C═N/N-O multiple bonds cleavage and recombination.
View Article and Find Full Text PDFOxidative Remote Aryl Rearrangement of -Cinnamyl--alkoxybenzyl Sulfonamides Using Hypervalent Iodine(III).
Org Lett
October 2024
Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
An oxidative remote aryl rearrangement of -cinnamyl--alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.
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