Supramolecular chemistry under mechanochemical conditions: a small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction,Chemical Science

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Supramolecular chemistry under mechanochemical conditions: a small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction
Chemical Science ( IF 7.6 ) Pub Date : 2020/03/10 , DOI: 10.1039/c9sc05823k
Shweta P Yelgaonkar ₁ , Dale C Swenson ₁ , Leonard R MacGillivray ₁

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We describe the integration of a small-molecule hydrogen-bond-donor template into a cascade reaction that is comprised of a combination of molecular and supramolecular events. The cascade is performed mechanochemically and in the presence of μL amounts of water. The small-molecule template is generated (molecular) using water-assisted vortex grinding and is then used to assemble an alkene (supramolecular) to undergo an intermolecular [2 + 2] photodimerization reaction (molecular). The chemical cascade results in a cyclobutane photoproduct that we show serves as a building block of a hydrogen-bonded network with a topology that conforms to T-silica. Remarkably, the molecular–supramolecular–molecular chemical cascade occurs stepwise and entirely regioselectively within the continuous mechanochemical conditions employed.

中文翻译：

机械化学条件下的超分子化学：生成小分子模板并整合到分子到超分子和回到分子级联反应中

我们描述了将小分子氢键供体模板整合到由分子和超分子事件组合组成的级联反应中。该级联是在微升水存在下以机械化学方式进行的。使用水辅助涡旋研磨生成小分子模板（分子），然后用于组装烯烃（超分子）以进行分子间[2 + 2]光二聚反应（分子）。化学级联产生了环丁烷光产物，我们展示了它作为氢键网络的构建块，其拓扑结构符合 T-二氧化硅。值得注意的是，分子-超分子-分子化学级联在所采用的连续机械化学条件下逐步且完全区域选择性地发生。

更新日期：2020-04-01

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