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. 2025 Feb 14;90(6):2372-2385.
doi: 10.1021/acs.joc.4c02892. Epub 2025 Feb 5.

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

Weigang Xu  1 , Pengfei Li  1 , Yuerong Li  1 , Zhangwen Kou  1 , Kaiyu Li  1 , Hengqi Li  1 , Sajjad Ali  1 , Junfeng Pan  2 , Zhengshen Wang  1 , Huaiji Zheng  1
Affiliations

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

Weigang Xu et al. J Org Chem. .

Abstract

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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