Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 22, Pages 3945-3949Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701072
Keywords
acyl radical; radical cyclization; visible light; tandem; photocatalysis
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Funding
- Institute for Basic Science [IBS-R010-G1]
- Ministry of Science & ICT (MSIT), Republic of Korea [IBS-R010-D1-2017-A00] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- National Research Foundation of Korea [21A20151513223] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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.
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