Visible-light-mediated radical cascade reaction: synthesis of 3-bromocoumarins from alkynoates

A visible-light-mediated radical addition of alkynoates to generate 3-bromocoumarins by using N-bromosuccinimide as the bromo source has been accomplished. This procedure provides a bromo radical addition/spirocyclization/ester migration cascade reaction under very mild reaction conditions without u...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 41; pp. 8820 - 8826
Main Authors Feng, Shangbiao, Li, Jinlai, Liu, Zaimin, Sun, Haiyu, Shi, Hongliang, Wang, Xiaolei, Xie, Xingang, She, Xuegong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
METAL-FREE CONDITIONS
ACIDS
1,3-HALOGEN MIGRATION
BOND FORMATION
ORGANIC HALIDES
CYCLIZATION
PHOTOREDOX CATALYSIS
COUMARIN DERIVATIVES
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Summary:A visible-light-mediated radical addition of alkynoates to generate 3-bromocoumarins by using N-bromosuccinimide as the bromo source has been accomplished. This procedure provides a bromo radical addition/spirocyclization/ester migration cascade reaction under very mild reaction conditions without using any catalyst or strong oxidant and does not need high reaction temperature. Furthermore, the reaction can also be enlarged to the gram scale, and the product 3-bromocoumarins can be further applied in the synthesis of complex compounds.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02199b