A practical electrophilic aminoselenation of -homoallyl benzimidate with diselenides promoted by PhICl/CuO has been developed. The easily available and stable diselenides were used as selenium sources. Various selenyl 1,3-oxazines, which are important frameworks in medicinal and biological chemistry, were easily obtained in moderate to good yields for the first time. Easy scaleup and scalability make this method attractive for the preparation of other valuable organoselenides.
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http://dx.doi.org/10.1039/d1cc04854f | DOI Listing |
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 PDFOrg Lett
November 2024
School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Herein, we report a AgF-mediated regio- and stereoselective acetoxyselenylation of terminal/internal alkynes from iodobenzene dicarboxylate [PhI(OCOR)] and diorganyl diselenides via multiple-site functionalization to afford β-selenyl enol esters in good yields. Alkynes derived from bioactive molecules, such as l(-)-borneol, l-menthol, and acyne oxalate, are also suitable for this transformation and afford the expected compounds.
View Article and Find Full Text PDFAngew 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 PDFActa Crystallogr E Crystallogr Commun
September 2024
University of Science Vietnam National University, Hanoi, 334 Nguyen Trai Thanh Xuan Hanoi 100000 Vietnam.
A new pyridine-fused seleno-diazo-lium salt, 3-(phenyl-selan-yl)[1,2,4]selena-diazolo[4,5-]pyridin-4-ylium chloride di-chloro-methane 0.352-solvate, CHNSe ·Cl·0.352CHCl, was obtained from the reaction between 2-pyridyl-selenenyl chloride and phenyl-seleno-cyanate.
View Article and Find Full Text PDFOrg Biomol Chem
September 2024
Guangxi Key Laboratory of Drug Discovery and Optimization, Guangxi Engineering Research Center for Pharmaceutical Molecular Screening and Druggability Evaluation, Key Laboratory of Medical Biotechnology and Translational Medicine, School of Pharmacy, Guilin Medical University, Guilin 541199, Guangxi, China..
A simple and efficient method to access 4-selenyl-isocoumarin derivatives through visible-light-promoted selenylation/cyclization of -(1-alkynyl) benzoates has been developed. This transformation is performed under mild conditions and has the advantages of functional group tolerance and broad substrate scope.
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