Iodonium Ion-Induced Cyclization and Aryl Migration of ortho-Hydroxystilbenes for the Synthesis of 3‑Aryl-2,3-dihydrobenzofuran

A facile and versatile protocol for the efficient synthesis of 3-aryl-2,3-dihydrobenzofuran (ADB) has been reported first. This reaction features the cyclization and aryl migration reaction of ortho-hydroxystilbene in ethanol, which is mediated by an iodonium ion, under ambient conditions. A class o...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 16; pp. 11460 - 11472
Main Authors Chen, Ying, Fan, Yiyao, Li, Yanqiu, Yao, Chunsuo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLIGOSTILBENES
INSERTION
GENERATION
MEDIATED OXIDATIVE CYCLIZATION
VITIS-AMURENSIS
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Summary:A facile and versatile protocol for the efficient synthesis of 3-aryl-2,3-dihydrobenzofuran (ADB) has been reported first. This reaction features the cyclization and aryl migration reaction of ortho-hydroxystilbene in ethanol, which is mediated by an iodonium ion, under ambient conditions. A class of ADB was prepared efficiently in good to excellent yields. Mechanism investigation revealed that acids and alcohols facilitated aryl migration, but alkaline and non-alcohol solvents promoted β elimination. The practicality of this strategy was further substantiated by two scale-up reactions and demonstrated in efficient synthetic elaboration.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00440