Intermolecular On-Surface σ-Bond Metathesis,Journal of the American Chemical Society

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Intermolecular On-Surface σ-Bond Metathesis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-05-03 00:00:00 , DOI: 10.1021/jacs.7b02430
Hong-Ying Gao _{1,

2} , Philipp Alexander Held , Saeed Amirjalayer _{1,

2} , Lacheng Liu _{1,

2} , Alexander Timmer _{1,

2} , Birgitta Schirmer , Oscar Díaz Arado _{1,

2} , Harry Mönig _{1,

2} , Christian Mück-Lichtenfeld , Johannes Neugebauer , Armido Studer , Harald Fuchs _{1,

2}

Affiliation

Silylation and desilylation are important functional group manipulations in solution-phase organic chemistry that are heavily used to protect/deprotect different functionalities. Herein, we disclose the first examples of the σ-bond metathesis of silylated alkynes with aromatic carboxylic acids on the Ag(111) and Au(111) surfaces to give the corresponding terminal alkynes and silyl esters, which is supported by density functional theory calculations and further confirmed by X-ray photoelectron spectroscopy analysis. Such a protecting group strategy applied to on-surface chemistry allows self-assembly structures to be generated from molecules that are inherently unstable in solution and in the solid state. This is shown by the successful formation of self-assembled hexaethynylbenzene at Ag(111). Furthermore, it is also shown that on the Au(111) surface this σ-bond metathesis can be combined with Glaser coupling to fabricate covalent polymers via a cascade process.

中文翻译：

分子间表面σ键复分解

甲硅烷基化和甲硅烷基化是溶液相有机化学中重要的官能团操作，其被大量用于保护/脱保护不同的官能团。在这里，我们公开了在Ag（111）和Au（111）表面上与芳族羧酸进行甲硅烷基化炔烃的σ键复分解的第一个实例，从而给出了相应的末端炔烃和甲硅烷基酯，这在密度泛函理论计算的支持下得以实现。并通过X射线光电子能谱分析进一步证实。应用于表面化学的这种保护基策略允许从在溶液和固态中固有地不稳定的分子产生自组装结构。这可以通过在Ag（111）上成功形成自组装的六乙炔基苯来证明。此外，

更新日期：2017-05-11

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