Effects of water addition on a catalytic fluorination of dienamine

Daiki Kuraoku, Tsunaki Yonamine, Genta Koja, Norio Yoshida, Satoru Arimitsu, Masahiro Higashi

Research output: Contribution to journalArticle

Abstract

We investigate the effects of water addition on a highly stereocontrolled fluorination of dienamine generated by α-branched enals and 60-hydroxy-9-amino-9-deoxy-epi-quinidine with N-fluorobenzenesulfonimide (NFSI) in the presence of Brønsted acid both experimentally and theoretically. It is experimentally found that water addition to organic solvent significantly shortens the reaction time whereas excessive water addition decreases the enantiomeric excess. The results calculated with three-dimensional reference interaction site model self-consistent field (3D-RISM-SCF) method are in good agreement with the experimental ones. It is revealed that the shortness of reaction time is caused by the reactant destabilization and that the decrease in enantiomeric excess is due to the difference of hydration free energy between two transition states.

Original languageEnglish
Article number3428
JournalMolecules
Volume24
Issue number19
DOIs
Publication statusPublished - Sep 21 2019

Fingerprint

Fluorination
fluorination
Halogenation
reaction time
self consistent fields
Water
water
Quinidine
destabilization
Hydration
Organic solvents
Free energy
hydration
free energy
acids
Acids
interactions

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Kuraoku, D., Yonamine, T., Koja, G., Yoshida, N., Arimitsu, S., & Higashi, M. (2019). Effects of water addition on a catalytic fluorination of dienamine. Molecules, 24(19), [3428]. https://doi.org/10.3390/molecules24193428

Effects of water addition on a catalytic fluorination of dienamine. / Kuraoku, Daiki; Yonamine, Tsunaki; Koja, Genta; Yoshida, Norio; Arimitsu, Satoru; Higashi, Masahiro.

In: Molecules, Vol. 24, No. 19, 3428, 21.09.2019.

Research output: Contribution to journalArticle

Kuraoku, D, Yonamine, T, Koja, G, Yoshida, N, Arimitsu, S & Higashi, M 2019, 'Effects of water addition on a catalytic fluorination of dienamine', Molecules, vol. 24, no. 19, 3428. https://doi.org/10.3390/molecules24193428
Kuraoku, Daiki ; Yonamine, Tsunaki ; Koja, Genta ; Yoshida, Norio ; Arimitsu, Satoru ; Higashi, Masahiro. / Effects of water addition on a catalytic fluorination of dienamine. In: Molecules. 2019 ; Vol. 24, No. 19.
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