Synthesis and Analysis of (γ,γ',γ''-Trifluoro)neopentyl (TFNP) Aryl Ethers as a Polar Fluoroaliphatic Motif

Author(s)

Tarui, Atsushi ; Piscelli, Bruno A. ; Al-Maharik, Nawaf ; Stewart, Josephine M. ; Niemcova, Patricie ; Cordes, David B. ; Mckay, Aidan P. ; Murphy, Cormac D. ; Cormanich, Rodrigo A. ; Hagan, David O'

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 30, n. 57, p. 5-pg., 2024-09-24.

Abstract

A route is developed to (gamma,gamma',gamma'''-trifluoro)neopentyl (TFNP) aryl ethers to extend the methods for the introduction of the tert-butyl group, carrying a fluorine on each of the methyl substituents. The route combines neopentyltosylate 3 with phenols and thiophenols to give efficient substitution reactions to the corresponding TFNP aryl ethers. The three C-F bonds adopt a helical propeller conformation as revealed by computation and single crystal X-ray structure analysis. The LogPs of TFNP ethers are lower (more hydrophilic) than their neopentyl analogues. The metabolism of selected TFNP ethers was explored in the fungus Cunninghamella elegans. (AU)

• FAPESP's process: 22/10156-7 - Experimental and Theoretical study of stereoelectronic effects and supramolecular assembly of organofluorinated compounds
• Grantee: Bruno de Almeida Piscelli
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 23/14064-2 - Modeling the Interaction of Janus-Face Cyclohexanes with dsDNA and ssDNA
• Grantee: Bruno de Almeida Piscelli
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate (Direct)
• FAPESP's process: 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches
• Grantee: Rodrigo Antonio Cormanich
• Support Opportunities: Research Grants - Young Investigators Grants