Visible-light-mediated cascade difunctionalization/cyclization of alkynoates with acyl chlorides for synthesis of 3-acylcoumarins

[Display omitted] •The radical cyclization affords 3-acylcoumarins from alkynoates and acyl chlorides.•A visible-light-mediated strategy for direct difunctionalization of alkynoates.•A variety of high bioactive 3-acylcoumarins were obtained.•This reaction involves radical acylation, 5-exo-trig cycli...

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Bibliographic Details
Published in:Tetrahedron letters 2018-05, Vol.59 (21), p.2038-2041
Main Authors: Liu, Yu, Wang, Qiao-Lin, Zhou, Cong-Shan, Xiong, Bi-Quan, Zhang, Pan-Liang, Kang, Shuang-Jian, Yang, Chang-An, Tang, Ke-Wen
Format: Article
Language:English
Subjects:
3-Acylcoumarin
Alkynoate
Difunctionalization
Radical cyclization
Visible light photoredox catalysis
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Summary:[Display omitted] •The radical cyclization affords 3-acylcoumarins from alkynoates and acyl chlorides.•A visible-light-mediated strategy for direct difunctionalization of alkynoates.•A variety of high bioactive 3-acylcoumarins were obtained.•This reaction involves radical acylation, 5-exo-trig cyclization and ester migration. A new visible-light-mediated radical cyclization of alkynoates with acyl chlorides is described for the one-pot construction of diverse 3-acylcoumarins with high efficiency and selectivity. This method is successful by sequential difunctionalization of an alkynes CC triple bond with the CCl bonds of acyl chloride and aromatic C(sp2)H bonds. The cyclization is proposed to simultaneously form two new carbon–carbon bonds, and involves radical acylation, 5-exo-trig cyclization, and ester migration.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.04.033