Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions

Chun Liang Lai, Hon Man Lee, Ching Han Hu

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Abstract

The mechanism of N-heterocyclic carbene (NHC) catalyzed transesterification reactions have been studied using density functional theory. Our study shows that the role of NHC is to assist proton transfer from alcohol to the carbonyl oxygen, forming the tetrahedral intermediate, which then decomposes to the acylated product. Our predicted activation energies are in fine agreement with the observed reaction rates. An alternative approach, which uses the tetrahedral intermediate as the transition state mimic, provides satisfactory predictions.

Original languageEnglish
Pages (from-to)6265-6270
Number of pages6
JournalTetrahedron Letters
Volume46
Issue number37
DOIs
Publication statusPublished - 2005 Sep 12

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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