Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

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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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-05
DOI
https://doi.org/10.1021/acs.joc.4c02892
Citations
1
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.94

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Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

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article

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

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article en
1 citations

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.

The Journal of Organic ChemistryVol. 90(6)
Northwest A&F University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 29%
Oxidative Organic Chemistry Reactions
0.94
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