Visible-light-enabled spirocyclization of alkynes leading to 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones

A mild and convenient visible-light-induced method has been developed for the construction of 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones through metal-free difunctionalization of alkynes with sulfinic acids or thiols at room temperature. The present protocol simply utilizes visible light as th...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2017, Vol.19 (23), p.568-5613
Main Authors: Wei, Wei, Cui, Huanhuan, Yang, Daoshan, Yue, Huilan, He, Chenglong, Zhang, Yulong, Wang, Hua
Format: Article
Language:English
Subjects:
Alkynes
Green chemistry
Light effects
Sulfur
Thiols
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Summary:A mild and convenient visible-light-induced method has been developed for the construction of 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones through metal-free difunctionalization of alkynes with sulfinic acids or thiols at room temperature. The present protocol simply utilizes visible light as the safe and eco-friendly energy source, and inexpensive and non-toxic organic dyes (Eosin Y and Na 2 -Eosin Y) as photocatalysts providing various sulfur-containing azaspiro[4,5]trienones in moderate to good yields. A visible-light-induced strategy has been established for the synthesis of 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones at room temperature in air.
ISSN:1463-9262
1463-9270
DOI:10.1039/c7gc02330h