Journal article

Modulation of Prins Cyclization by Vibrational Strong Coupling

Kenji Hirai, Rie Takeda, James A Hutchison, Hiroshi Uji-i

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | WILEY-V C H VERLAG GMBH | Published : 2020

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 proportion..

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University of Melbourne Researchers

Grants

Awarded by JST PRESTO


Awarded by JSPS KAKENHI


Awarded by Australian Research Council (ARC) Future Fellowship


Awarded by ARC Centre of Excellence in Exciton Science


Funding Acknowledgements

This work was supported by JST PRESTO (JPMJPR18TA) and JSPS KAKENHI (Grant Nos. JP18K19085), and partially supported by the JSPS Core-to-Core Program A. Advanced Research Networks. J.A.H. acknowledges the support of an Australian Research Council (ARC) Future Fellowship (FT180100295) and the ARC Centre of Excellence in Exciton Science (CE170100026).