Visible Light-Promoted Synthesis of Spiroepoxy Chromanone Derivatives via a Tandem Oxidation/Radical Cyclization/Epoxidation Process

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A highly efficient and straightforward approach for the synthesis of spiroepoxy chroman-4-one derivatives was developed using a visible light-enabled tandem radical strategy. The reaction is initiated by the formation of an acyl radical that undergoes intramolecular radical cyclization and epoxidation. The optimal result was obtained with 1 mol% of Ru(bpy)(3)Cl(2)6H(2)O, TBHP, and K2CO3 in i-PrOAc at room temperature with irradiation from a blue LED. This unprecedented tandem approach utilizes a broad range of substrates, and provides a convenient and powerful synthetic tool for accessing the synthetically useful spiroepoxy chroman-4-ones and their nitrogen-containing derivatives.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2017-11
Language
English
Article Type
Article
Keywords

CATALYZED CARBONYLATION-PEROXIDATION; C-H BONDS; PHOTOREDOX CATALYSIS; RADICAL REACTIONS; ORGANIC-SYNTHESIS; DIRECT ACCESS; ALKENES; ALDEHYDES; KETONES; CHROMAN-4-ONE

Citation

ADVANCED SYNTHESIS & CATALYSIS, v.359, no.22, pp.3945 - 3949

ISSN
1615-4150
DOI
10.1002/adsc.201701072
URI
http://hdl.handle.net/10203/237184
Appears in Collection
CH-Journal Papers(저널논문)
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