Selenium dioxide promoted dinitrogen extrusion/direct selenation of arylhydrazines and anilines

A novel, efficient, economical strategy for the coupling and direct selenation of arylhydrazines to selenides using SeO2 has been developed. Our method employs SeO2 as the selenium source with hydrazines as coupling reactants to generate selenides via dinitrogen extrusion. This reagent also helped t...

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Veröffentlicht in:Tetrahedron 2020-04, Vol.76 (16), p.131105, Article 131105
Hauptverfasser: Yaqoob Bhat, Mohammad, Kumar, Atul, Naveed Ahmed, Qazi
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Sprache:eng
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Zusammenfassung:A novel, efficient, economical strategy for the coupling and direct selenation of arylhydrazines to selenides using SeO2 has been developed. Our method employs SeO2 as the selenium source with hydrazines as coupling reactants to generate selenides via dinitrogen extrusion. This reagent also helped to generate ArSe substitued aniline derivatives via C–H functionalization reaction in good yields. The application of this method in gram scale was also carried out. [Display omitted] •A novel, efficient, economical strategy for the direct selenation of arylamines and hydrazines to selenides using SeO2 was successfully developed.•Our reaction revealed a good functional group tolerance and proceeded well with variation in the electronic nature of Anilines and Phenylhydrazines.•This reagent is compatible with hydrazines and helps to promotes unusual dinitrogen extrusion assisted selenation reaction in good yields.•The application of our work is the gram scale synthesis and extension to β-napthol.•Application of this approach towards Selenation of β-Napthol.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131105