Modulation of Prins Cyclization by Vibrational Strong Coupling.,Angewandte Chemie International Edition

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Modulation of Prins Cyclization by Vibrational Strong Coupling.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-22 , DOI: 10.1002/anie.201915632
Kenji Hirai _{1,

2,

3} , Rie Takeda _{1,

2} , James A Hutchison ₄ , Hiroshi Uji-I _{1,

3,

5}

Affiliation

Light-molecule strong coupling has emerged within the last decade as a new method to control chemical reactions. A few years ago it was discovered that chemical reactivity could be altered by vibrational strong coupling (VSC). Only a limited number of reactions have been investigated under VSC to date, including solvolysis and deprotection reactions. Here the effect of VSC on a series of aldehydes and ketones undergoing Prins cyclization, an important synthetic step in pharmaceutical chemistry, is investigated. A decrease of the second-order rate constant with VSC of the reactant carbonyl stretching groups is observed. We also observe an increased activation energy due to VSC, but proportional changes in activation enthalpy and entropy, suggesting no substantive change in reaction pathway. The addition of common cycloaddition reactions to the stable of VSC-modified chemical reactions is another step towards establishing VSC as a genuine tool for synthetic chemistry.

中文翻译：

振动强耦合对小蛋白环的调节。

在过去的十年中，轻分子强耦合已成为控制化学反应的新方法。几年前，人们发现通过振动强耦合（VSC）可以改变化学反应性。迄今为止，在VSC下仅研究了有限数量的反应，包括溶剂分解和脱保护反应。在这里，研究了VSC对一系列进行Prins环化的醛和酮的作用，这是药物化学中重要的合成步骤。观察到反应物羰基拉伸基团的二阶速率常数随VSC降低。我们还观察到由于VSC引起的活化能增加，但是活化焓和熵呈比例变化，表明反应途径没有实质性变化。

更新日期：2020-02-18

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