Aziridine used as a vinylidene unit in palladium-catalyzed [2+2+1] domino annulation

A novel palladium-catalyzed three-component reaction of 3-iodochromones with bridged olefins and aziridine is described, which employs a [2 + 2 + 1] domino annulation strategy to produce chromone fused methylenecyclopentanes in moderate to good yields via a Heck coupling/C(sp(2))-H activation/imine-...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 13; pp. 3413 - 3420
Main Authors Zhu, Wen-Qing, Zhang, Zi-Wei, Han, Wen-Yong, Fang, Yu-Chen, Yang, Ping, Li, Lin-Qiang, Chen, Yong-Zheng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 29.06.2021
Royal Society of Chemistry
Subjects
Alkenes
Chemical reactions
Chemistry
Chemistry, Organic
Crystallography
Organic chemistry
Palladium
Physical Sciences
Science & Technology
Single crystals
Vinylidene
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Summary:A novel palladium-catalyzed three-component reaction of 3-iodochromones with bridged olefins and aziridine is described, which employs a [2 + 2 + 1] domino annulation strategy to produce chromone fused methylenecyclopentanes in moderate to good yields via a Heck coupling/C(sp(2))-H activation/imine-enamine tautomerization/retro-aza-Michael addition sequence. Significantly, aziridine was used as a vinylidene unit by cleavage of two C-N bonds and was successfully introduced into the products for the first time.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo00458a