論文

査読有り 筆頭著者 責任著者 国際共著 国際誌
2020年1月22日

Modulation of Prins Cyclization by Vibrational Strong Coupling.

Angewandte Chemie (International ed. in English)
  • Kenji Hirai
  • ,
  • Rie Takeda
  • ,
  • James A Hutchison
  • ,
  • Hiroshi Uji-I

59
開始ページ
5332
終了ページ
5335
記述言語
英語
掲載種別
DOI
10.1002/anie.201915632

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.

リンク情報
DOI
https://doi.org/10.1002/anie.201915632
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/31970847
ID情報
  • DOI : 10.1002/anie.201915632
  • PubMed ID : 31970847

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