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

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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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-04, Vol.60 (33), p.4455-4458
Hauptverfasser: 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
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Sprache:eng
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Cycloaddition
Cyclobutane
Heterocyclic compounds
Substrates
Thioxanthenone
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container_issue 33
container_start_page 4455
container_title Chemical communications (Cambridge, England)
container_volume 60
creator 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
description 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.
doi_str_mv 10.1039/d4cc00690a
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Cycloaddition
Cyclobutane
Heterocyclic compounds
Substrates
Thioxanthenone
title Construction of cyclobutane-fused tetracyclic skeletons via substrate-dependent EnT-enabled dearomative [2+2] cycloaddition of benzofurans (benzothiophenes)/maleimides
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