Nucleophilic Radiofluorination Using Tri-tert-Butanol Ammonium as a Bifunctional Organocatalyst: Mechanism and Energetics
Oh YH, Shinde SS, Lee S (2022)
Publication Type: Journal article
Publication year: 2022
Journal
Book Volume: 27
Journal Issue: 3
DOI: 10.3390/molecules27031044
Abstract
We present a quantum chemical analysis of the F-18-fluorination of 1,3-ditosylpropane, promoted by a quaternary ammonium salt (tri-(tert-butanol)-methylammonium iodide (TBMA-I) with moderate to good radiochemical yields (RCYs), experimentally observed by Shinde et al. We obtained the mechanism of the S(N)2 process, focusing on the role of the -OH functional groups facilitating the reactions. We found that the counter-cation TBMA(+) acts as a bifunctional promoter: the -OH groups function as a bidentate 'anchor' bridging the nucleophile [F-18]F- and the -OTs leaving group or the third -OH. These electrostatic interactions cooperate for the formation of the transition states of a very compact configuration for facile S(N)2 F-18-fluorination.
Involved external institutions
Korea, Republic of (KR)How to cite
APA:
Oh, Y.-H., Shinde, S.S., & Lee, S. (2022). Nucleophilic Radiofluorination Using Tri-tert-Butanol Ammonium as a Bifunctional Organocatalyst: Mechanism and Energetics. Molecules, 27(3). https://dx.doi.org/10.3390/molecules27031044
MLA:
Oh, Young-Ho, Sandip S. Shinde, and Sungyul Lee. "Nucleophilic Radiofluorination Using Tri-tert-Butanol Ammonium as a Bifunctional Organocatalyst: Mechanism and Energetics." Molecules 27.3 (2022).
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