Isoselenazole Synthesis by Rh-Catalyzed Direct Annulation of Benzimidates with Sodium Selenite

Organoselenium compounds have attracted significant research interest because of their potent therapeutic activities and indispensable applications in the organic chemistry field. The selenation reactions conventionally rely on the use of sensitive Se reagents; thus, new synthetic methods with impro...

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Published inChemistry an international journal Vol. 5; no. 4; pp. 2068 - 2074
Main Authors Xu-Xu, Qing-Feng, Nishii, Yuji, Miura, Masahiro
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.09.2023
Subjects
Acids
annulation
Catalysis
Chemical reactions
Chemical synthesis
Chemistry
Chromatography
C–H bond cleavage
direct coupling
NMR
Nuclear magnetic resonance
Organic chemistry
organoselenium compound
Organoselenium compounds
Reagents
Selenites
Selenium
Sodium
Solvents
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Summary:Organoselenium compounds have attracted significant research interest because of their potent therapeutic activities and indispensable applications in the organic chemistry field. The selenation reactions conventionally rely on the use of sensitive Se reagents; thus, new synthetic methods with improved efficiency and operational simplicity have recently been of particular interest. In this manuscript, we report a Rh-catalyzed direct selenium annulation using tractable sodium selenite (Na2SeO3) as the limiting reagent. The selenite species was converted to highly electrophilic SeO(OBz)2 in situ upon treatment with Bz2O, thereby undergoing C–H/N–H double nucleophilic selenation. A series of benzimidates successfully underwent selenation under mild reaction conditions to afford isoselenazole derivatives.
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ISSN:2624-8549
2624-8549
DOI:10.3390/chemistry5040140