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Modulation of Prins Cyclization by Vibrational Strong Coupling

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Title: Modulation of Prins Cyclization by Vibrational Strong Coupling
Authors: Hirai, Kenji Browse this author →KAKEN DB
Takeda, Rie Browse this author
Hutchison, James A. Browse this author
Uji-i, Hiroshi Browse this author →KAKEN DB
Keywords: cyclizations
infrared spectroscopy
Rabi splitting
vibrational strong coupling
Issue Date: 23-Mar-2020
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Publisher DOI: 10.1002/anie.201915632
Abstract: 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.
Rights: This is the peer reviewed version of the following article: K. Hirai, R. Takeda, J. A. Hutchison, H. Uji-i, Angew. Chem. Int. Ed. 2020 , 59 , 5332, which has been published in final form at . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: article (author version)
Appears in Collections:電子科学研究所 (Research Institute for Electronic Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 平井 健二

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