Esterification of Tertiary Amides by Alcohols Through C−N Bond Cleavage over CeO2

Takashi Toyao, Md Nurnobi Rashed, Yoshitsugu Morita, Takashi Kamachi, S. M.A. Hakim Siddiki, Md A. Ali, A. S. Touchy, Kenichi Kon, Zen Maeno, Kazunari Yoshizawa, Ken ichi Shimizu

研究成果: Contribution to journalArticle査読

12 被引用数 (Scopus)

抄録

CeO2 has been found to promote ester forming alcoholysis reactions of tertiary amides. The present catalytic system is operationally simple, recyclable, and it does not require additives. The esterification process displays a wide substrate scope (>45 examples; up to 93 % isolated yield). Results of a density functional theory (DFT) study combined with in situ FT-IR observations indicate that the process proceeds through rate limiting addition of a CeO2 lattice oxygen to the carbonyl group of the adsorbed acetamide species with energy barrier of 17.0 kcal/mol. This value matches well with experimental value (17.9 kcal/mol) obtained from analysis of the Arrhenius plot. Further studies by in situ FT-IR and temperature programmed desorption using probe molecules demonstrate that both acidic and basic properties are important, and consequently, CeO2 showed the best performance for the C−N bond cleavage reaction.

本文言語英語
ページ(範囲)449-456
ページ数8
ジャーナルChemCatChem
11
1
DOI
出版ステータス出版済み - 1 9 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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