在可见光辐照下，通过金（I）催化邻烷基苯甲酸的炔基环化作用生成 3-炔基苯酞。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

The Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1021/acs.joc.4c01876

María Ballarín-Marión, Jorge C Herrera-Luna, Vincent Corcé, Héloïse Dossmann, Cyril Ollivier, Virginie Mouriès-Mansuy, Louis Fensterbank

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引用次数: 0

摘要

在此，我们报告了一个 Csp2-Csp 交叉偶联过程，该过程涉及金催化与可见光光催化的合并，导致邻炔基苯甲酸的炔基环化。以 E:Z 异构体混合物的形式获得了相应的、以前未曾描述过的亚烷基酞产品。关键的 C-C 键的形成是基于炔基碘化物与乙烯基金（I）中间体的氧化加成的光活化，而乙烯基金（I）中间体是由最初的 5-exo-dig 环化途径产生的，这一点得到了包括 DFT 计算在内的机理研究的支持。

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Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation.

Herein, we report a Csp²-Csp cross-coupling process involving the merger of gold catalysis and visible light photocatalysis leading to the alkynylative cyclization of o-alkynyl benzoic acids. The corresponding and previously undescribed alkynylidenephthalide products were obtained as mixtures of E:Z isomers. The key C-C bond formation is based on the photoactivation of the oxidative addition of an alkynyliodide to a vinylgold(I) intermediate resulting from an initial 5-exo-dig cyclization pathway, as supported by mechanistic studies including DFT calculations.

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来源期刊

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.