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

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-10-18 Epub Date: 2024-10-07 DOI:10.1021/acs.joc.4c02009
Johanna Frey, Jean-Philippe Goddard, Morgan Cormier
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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.

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利用近红外光催化技术催化炔二钴六羰基络合物的脱保护作用。
二钴六羰基络合物因其在尼古拉斯反应中的应用而闻名,或者仅仅作为炔的保护基。要回收炔烃,必须进行脱金属处理,通常需要使用一定量的氧化剂或强配体。本文报告了一种基于光催化过程的脱金属方法。这种方法在有氧条件下使用光催化剂,并通过温和的近红外辐照获得最佳效果。此外,还介绍了一项机理研究,以阐明光催化系统是如何促进这种脱保护作用的。这种工具与炔烃的一锅反应和正交脱保护兼容,为进一步的应用提供了新的前景。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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