Iodide-Dependent Selective Dehydroaromatization Affording Maleimide-Fused 9,10-Phenanthrenes and Their Analogues

A novel and selective synthesis of polycyclic fused maleimides from easily available raw materials under metal-free conditions is presented. This cascade protocol involves self-condensation of cyclohexanones, followed by Diels–Alder reaction with maleimides, intramolecular dehydration, and selective...

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Veröffentlicht in:	Organic letters 2023-10, Vol.25 (39), p.7142-7147
Hauptverfasser:	Wang, Shuowen, Chen, Zhuohao, Chen, Shanping, Shao, Wen, Chen, Ya, Deng, Guo-Jun
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creator	Wang, Shuowen Chen, Zhuohao Chen, Shanping Shao, Wen Chen, Ya Deng, Guo-Jun
description	A novel and selective synthesis of polycyclic fused maleimides from easily available raw materials under metal-free conditions is presented. This cascade protocol involves self-condensation of cyclohexanones, followed by Diels–Alder reaction with maleimides, intramolecular dehydration, and selective dehydroaromatization in a one-pot fashion, affording maleimide-fused 9,10-phenanthrenes and their analogues in satisfactory yields. Notably, iodide reagents play a critical role in switching the selectivity toward full or partial dehydrogenation compounds.
doi_str_mv	10.1021/acs.orglett.3c02638
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title	Iodide-Dependent Selective Dehydroaromatization Affording Maleimide-Fused 9,10-Phenanthrenes and Their Analogues
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