Metal- and photocatalyst-free visible-light-promoted regioselective selenylation of coumarin derivatives via oxidation-induced C-H functionalization

A visible-light-promoted approach for the regioselective selenylation of 4-amino substituted coumarins has been developed under metal- and photocatalyst-free conditions at room temperature. Notably, dual selenylation products were also obtained selectively when N-substituted 4-(phenylamino)-2H-chrom...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 20; pp. 2974 - 2979
Main Authors Yang, Daoshan, Li, Guoqing, Xing, Chengyu, Cui, Wenwen, Li, Kexin, Wei, Wei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2018
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Coumarin
Organic chemistry
Oxidation
Photocatalysts
Physical Sciences
Regioselectivity
Science & Technology
Substitutes
ORGANIC-SYNTHESIS
SULFINIC ACIDS
HETEROARENES
MECHANISM
ENAMINONES
ORGANOSELENIUM COMPOUNDS
MEDIATED SYNTHESIS
BONDS
ARENES
SULFENYLATION
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Summary:A visible-light-promoted approach for the regioselective selenylation of 4-amino substituted coumarins has been developed under metal- and photocatalyst-free conditions at room temperature. Notably, dual selenylation products were also obtained selectively when N-substituted 4-(phenylamino)-2H-chromen-2-ones were employed. Preliminary mechanism studies suggest that oxidation-induced C-H functionalization may be involved in this transformation. The present method provides a highly attractive and alternative approach to C-Se bond formation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c8qo00899j