On-Surface Intramolecular Dehalogenation of Vicinal Dibromides for the Direct Formation of C–C Double Bonds,The Journal of Physical Chemistry C

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On-Surface Intramolecular Dehalogenation of Vicinal Dibromides for the Direct Formation of C–C Double Bonds
The Journal of Physical Chemistry C ( IF 3.3 ) Pub Date : 2019-12-06 , DOI: 10.1021/acs.jpcc.9b09713
Xin Yu ₁ , Haiping Lin ₂ , Yingke Yang ₂ , Liangliang Cai ₁ , Wei Xu ₁

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The intramolecular dehalogenation reaction as an essential step is generally involved in the deprotection of carbon–carbon double bonds in solution chemistry. However, harsh reaction conditions often limit the functional group compatibility and cause the selectivity problems. In comparison with traditional solution reactions, on-surface chemical reactions always occur on metal substrates, which could serve as catalysts to effectively reduce the reaction barriers in many cases. On the other hand, on-surface intermolecular dehalogenative homocoupling reactions have been extensively demonstrated, while, to our knowledge, intramolecular dehalogenation reactions are less discussed on surfaces. Herein, by the combination of high-resolution scanning tunneling microscopy imaging and density functional theory calculations, we introduce the vicinal dibromo group on chemically different surfaces, such as Cu(110), Ag(110), and Au(111), respectively, to investigate the generality of intramolecular dehalogenation reactions. As a result, we successfully achieved the direct formation of C–C double-bonded products in a facile manner on all three surfaces.

中文翻译：

邻二溴化物的分子内分子内脱卤作用，直接形成CC双键

分子内脱卤反应是必不可少的步骤，通常涉及溶液化学中碳-碳双键的脱保护。但是，苛刻的反应条件通常会限制官能团的相容性并导致选择性问题。与传统的溶液反应相比，表面化学反应总是在金属基材上发生，在许多情况下，表面化学反应可作为催化剂以有效减少反应障碍。另一方面，表面上的分子间脱卤均偶联反应已得到广泛证明，而据我们所知，分子内脱卤反应在表面上的讨论较少。在此，结合高分辨率扫描隧道显微镜成像和密度泛函理论计算，我们分别在化学上不同的表面上引入邻位二溴基团，例如Cu（110），Ag（110）和Au（111），以研究分子内脱卤反应的一般性。结果，我们成功地在所有三个表面上以简便的方式成功实现了CC双键产品的直接成型。

更新日期：2019-12-07

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