Regio- and Stereoselective Oxyiodination Reaction of Fluoroalkylated Internal Alkynes: An Easy Access to Fluoroalkylated, Multisubstituted Enol Derivatives

A concise and efficient protocol has been developed for regio- and <i>E</i>-selective oxyiodination of fluoroalkylated internal alkynes employing iodobenzene diacetate in conjunction with tetrabutylammonium iodide, enabling the synthesis of a diverse array of (3,3,3-trifluoro-2-iodopropen-1-yl)acetates. Subsequently, these oxyiodinated intermediates were subjected to standard Suzuki-Miyaura cross-coupling conditions, thereby furnishing fluoroalkylated, multisubstituted enol derivatives in good yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-11
DOI
https://doi.org/10.1021/acs.joc.5c01579
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Regio- and Stereoselective Oxyiodination Reaction of Fluoroalkylated Internal Alkynes: An Easy Access to Fluoroalkylated, Multisubstituted Enol Derivatives

Takao Saito, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Regio- and Stereoselective Oxyiodination Reaction of Fluoroalkylated Internal Alkynes: An Easy Access to Fluoroalkylated, Multisubstituted Enol Derivatives

Takao Saito, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno, Kaho Kasai
article en

Abstract

A concise and efficient protocol has been developed for regio- and <i>E</i>-selective oxyiodination of fluoroalkylated internal alkynes employing iodobenzene diacetate in conjunction with tetrabutylammonium iodide, enabling the synthesis of a diverse array of (3,3,3-trifluoro-2-iodopropen-1-yl)acetates. Subsequently, these oxyiodinated intermediates were subjected to standard Suzuki-Miyaura cross-coupling conditions, thereby furnishing fluoroalkylated, multisubstituted enol derivatives in good yields.

The Journal of Organic ChemistryVol. 90(46)
Kyoto Institute of Technology (JP)
Openalex Percentile: Top 71%
Fluorine in Organic Chemistry
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Regio- and Stereoselective Oxyiodination Reaction of Fluoroalkylated Internal Alkynes: An Easy Access to Fluoroalkylated, Multisubstituted Enol Derivatives — Takao Saito, Motohiro Yasui, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS