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Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne. | LitMetric
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Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne.

Weigang Xu Pengfei Li Yuerong Li Zhangwen Kou Kaiyu Li Hengqi Li Sajjad Ali Junfeng Pan Zhengshen Wang Huaiji Zheng

J Org Chem

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest Agriculture & Forestry University, 3 Taicheng Road, Yangling 712100, China.

Published: February 2025

A tandem Hexadehydro-Diels-Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which iodonium ylide served as a unique double bond and reacted with aryne to form a four-membered iodonium(III) cycle, then converted to iodoarene after aryl group migration from iodine to adjacent carbon. This strategy allows the efficient construction of fully substituted iodoarene compounds.

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 Source
http://dx.doi.org/10.1021/acs.joc.4c02892DOI Listing

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