Reductive Preparation of Fluoroalkyl Copper Complexes from Perfluorinated Alkyl Iodides Using Diboron

The reductive synthesis of fluoroalkyl copper phenanthroline complexes from fluoroalkyl iodides, using diboron as a reductant, is reported in this study. The structure of Cu(C<sub>4</sub>F<sub>9</sub>)(phen), isolated as a phosphine adduct, was confirmed by X-ray crystallography. These copper complexes underwent smooth cross-coupling with aryl iodides under mild conditions to afford fluoroalkylated arenes. Furthermore, a one-pot protocol enabled the reductive coupling of aryl iodides and fluoroalkyl iodides without the need to isolate the intermediate fluoroalkyl copper complexes.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-19
DOI
https://doi.org/10.1021/acs.joc.5c01513
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
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article

Reductive Preparation of Fluoroalkyl Copper Complexes from Perfluorinated Alkyl Iodides Using Diboron

H. NISHIGUCHI, Sensuke Ogoshi, Ryohei Doi
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Reductive Preparation of Fluoroalkyl Copper Complexes from Perfluorinated Alkyl Iodides Using Diboron

H. NISHIGUCHI, Sensuke Ogoshi, Ryohei Doi
article en

Abstract

The reductive synthesis of fluoroalkyl copper phenanthroline complexes from fluoroalkyl iodides, using diboron as a reductant, is reported in this study. The structure of Cu(C<sub>4</sub>F<sub>9</sub>)(phen), isolated as a phosphine adduct, was confirmed by X-ray crystallography. These copper complexes underwent smooth cross-coupling with aryl iodides under mild conditions to afford fluoroalkylated arenes. Furthermore, a one-pot protocol enabled the reductive coupling of aryl iodides and fluoroalkyl iodides without the need to isolate the intermediate fluoroalkyl copper complexes.

The Journal of Organic ChemistryVol. 90(39)
Applied Science Private University (JO), Faculty (United Kingdom) (GB), Tokyo Metropolitan University (JP), Graduate School USA (US), The University of Osaka (JP)
Openalex Percentile: Top 80%
Fluorine in Organic Chemistry
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