Catalytic Deprotection of Alkyne Dicobalt Hexacarbonyl Complexes using Near-Infrared Photocatalysis

Dicobalt hexacarbonyl complexes are well-known for their applications in the Nicholas reaction or simply as a protecting group for alkynes. To recover the alkyne, demetalation is necessary, which usually involves a stoichiometric amount of an oxidizing agent or a strong ligand. This article reports a demetalation methodology based on a photocatalytic process. This approach employs a photocatalyst under aerobic conditions, and the optimal results were achieved using mild near-infrared irradiation. A mechanistic investigation is also presented to elucidate how the photocatalytic system promotes this deprotection. This tool is compatible with the one-pot reaction and orthogonal deprotection of alkynes, offering new perspectives for further applications.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-07
DOI
https://doi.org/10.1021/acs.joc.4c02009
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.25

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article

Catalytic Deprotection of Alkyne Dicobalt Hexacarbonyl Complexes using Near-Infrared Photocatalysis

Morgan Cormier, Jean‐Philippe Goddard, Johanna Frey
1 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
0.25
article

Catalytic Deprotection of Alkyne Dicobalt Hexacarbonyl Complexes using Near-Infrared Photocatalysis

Morgan Cormier, Jean‐Philippe Goddard, Johanna Frey
article en
1 citations

Abstract

Dicobalt hexacarbonyl complexes are well-known for their applications in the Nicholas reaction or simply as a protecting group for alkynes. To recover the alkyne, demetalation is necessary, which usually involves a stoichiometric amount of an oxidizing agent or a strong ligand. This article reports a demetalation methodology based on a photocatalytic process. This approach employs a photocatalyst under aerobic conditions, and the optimal results were achieved using mild near-infrared irradiation. A mechanistic investigation is also presented to elucidate how the photocatalytic system promotes this deprotection. This tool is compatible with the one-pot reaction and orthogonal deprotection of alkynes, offering new perspectives for further applications.

The Journal of Organic ChemistryVol. 89(20)
Centre National de la Recherche Scientifique (FR), Université de Haute-Alsace (FR), Université de Strasbourg (FR)
Centre National de la Recherche Scientifique
Clean water and sanitation
Openalex Percentile: Top 48%
Radical Photochemical Reactions
0.25
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