Synthesis of Janus All-Cis Tetrafluorocyclohexanes Carrying 1,4-Diether Motifs

Author(s)

Poskin, Thomas J. ; Piscelli, Bruno A. ; Mckay, Aidan P. ; Cordes, David B. ; Eguchi, Yuto ; Yamada, Shigeyuki ; Cormanich, Rodrigo A. ; O'Hagan, David

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. N/A, p. 7-pg., 2024-11-27.

Abstract

Nucleophilic aromatic substitutions (SNAr) of alkoxides on pentafluoroaryl ethers are explored as a first step in a synthesis sequence to generate all-cis 2,3,5,6-tetrafluorocyclohexyl-1,4-dialkyl ethers 1. The SNAr reaction was explored both experimentally and theoretically to rationalize ortho/para/meta selectivities. tert-Butyl deprotection of products followed by phenol alkylations introduces versatility to the synthesis. The final Rh(CAAC) 3 catalyzed aryl hydrogenation step of intermediate tetrafluoroaryl-1,4-diethers generated cyclohexane products 1. This chemistry introduces a new class of Janus fluorocyclohexane derivatives with ether substituents placed 1,4- to each other. (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