Construction of cyclobutane-fused tetracyclic skeletons via substrate-dependent EnT-enabled dearomative [2+2] cycloaddition of benzofurans (benzothiophenes)/maleimides

Herein, a novel and facile organic photosensitizer (thioxanthone)-mediated energy-transfer-enabled (EnT-enabled) dearomative [2+2] cycloaddition of aromatic heterocycles/maleimides for green synthesis of cyclobutane-fused polycyclic skeletons is reported. Mechanistic investigations revealed that dif...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 33; pp. 4455 - 4458
Main Authors Liao, Zhi-Yu, Gao, Fan, Ye, Yu-Hang, Yu, Qian-Hui, Yang, Cui, Luo, Qing-Yu, Du, Fei, Pan, Bin, Zhong, Wen-Wu, Liang, Wu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.04.2024
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Cyclobutane
Heterocyclic compounds
Physical Sciences
Science & Technology
Substrates
Thioxanthenone
VISIBLE-LIGHT PHOTOCATALYSIS
PHOTOCYCLOADDITION
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Summary:Herein, a novel and facile organic photosensitizer (thioxanthone)-mediated energy-transfer-enabled (EnT-enabled) dearomative [2+2] cycloaddition of aromatic heterocycles/maleimides for green synthesis of cyclobutane-fused polycyclic skeletons is reported. Mechanistic investigations revealed that different EnT pathways by triplet thioxanthone were initiated when different aromatic heterocycles participated in the reaction, giving the corresponding excited intermediates, which underwent the subsequent intermolecular [2+2] cycloaddition to access the desired highly functionalized cyclobutane-fused polycyclic skeletons.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc00690a