ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Modulation of Prins Cyclization by Vibrational Strong Coupling

preprint
submitted on 18.12.2019, 07:42 and posted on 23.12.2019, 06:37 by Kenji Hirai, Rie Takeda, JAMES HUTCHISON, Hiroshi Uji-i
Light-molecule strong coupling has emerged within the last decade as an entirely new method to control chemical reactions. A few years ago it was discovered that the chemical reactivity could be altered by vibrational strong coupling (VSC). While the potential of VSC in organic chemistry appears enormous, only a limited number of reactions have been investigated under VSC to date, including solvolysis and deprotection reactions. Here we investigate the effect of VSC on a series of aldehydes and ketones undergoing Prins cyclization, an important synthetic step in pharmaceutical chemistry. We observe a decrease of the second-order rate constant with VSC of the reactant carbonyl stretching groups. We measure an increased activation energy due to VSC, but proportional changes in activation enthalpy and entropy suggest 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.

History

Email Address of Submitting Author

hirai@es.hokudai.ac.jp

Institution

Hokkaido University

Country

Japan

ORCID For Submitting Author

0000-0003-3307-3970

Declaration of Conflict of Interest

No conflict

Exports

Read the published paper

in Angewandte Chemie

ChemRxiv

Exports