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Organosulfur and Organoselenium Chemistry.
Molecules
November 2024
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Organosulfur- and organoselenium-containing compounds play a crucial role in organic synthesis [...
View Article and Find Full Text PDFDirect synthesis of α-functionalized amides via heteroatom-hydrogen insertion reactions using amide-sulfoxonium ylides.
Nat Commun
November 2024
Bioland Laboratory, Guangzhou, China.
α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput synthesis using amide-sulfoxonium ylides as carbene precursors in a Si-H, Ge-H, B-H, Se-H, and S-H insertion reactions to target a wide range of α-silyl, α-geryl, α-boryl, α-selenyl, and α-sulfur (hetero)amides. The process is featured as simple operation, mild conditions, broad substrate scope, high functional group compatibility, and excellent chemoselectivity.
View Article and Find Full Text PDFAsymmetric Carbene Insertion into Se-S Bonds by Synergistic Rh(II)/Guanidine Catalysis Involving Chalcogen-Bond Assistance.
Angew Chem Int Ed Engl
November 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
The efficient construction of chalcogen-atom-based chiral compounds remains a challenge, despite the importance of organoselenium and organosulfur compounds in life and materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report an enantioselective insertion platform to install a stereogenic center bearing selenyl and thiocyano functional groups.
View Article and Find Full Text PDFMechanistic Study on Selenium- and Sulfur-Mediated Isomerization of Hydroxamic Acids.
Chemistry
December 2023
Institute of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.
An in-depth computational study reveals the intriguing mechanism of the recently reported isomerization of hydroxamic acids into para-aminophenols catalyzed by phenylselenyl bromide under mild conditions. The computations not only align with the reported experimental data, effectively explaining observed phenomena such as para-selectivity but also shed light on crucial aspects of the reaction mechanism that establish limitations on the scope of the studied rearrangement. Additionally, a joint theoretical/experimental study was performed to examine the potency of the phenylsulfenyl bromide to mediate the reaction under the same conditions.
View Article and Find Full Text PDFOrganosulfur and Organoselenium Functionalized Benzimidazo[1,2-a]quinolines: From Experimental and Theoretical Photophysics to All-Solution-Processed OLEDs.
J Fluoresc
May 2024
Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande do Sul, 91501-970, Brazil.
In this study, we present the synthesis of benzimidazo[1,2-a] quinoline-based heterocycles bearing organosulfur and organoselenium moieties through transition-metal-free cascade reactions involving a sequential intermolecular aromatic nucleophilic substitution (SN). Both sulfur and selenium derivatives presented absorption maxima located around 355 nm related to spin and symmetry allowing electronic π-π* transitions, and fluorescence emission at the violet-blue region (~440 nm) with relatively large Stokes shift. The fluorescence quantum yields were slightly influenced by the chalcogen, with the sulfur derivatives presenting higher values than the selenium analogs.
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