Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest.

• Aryl trifluorovinylethers were used as precursors for preparing a diverse pool of hydro-/vinylfluoroethers. • Hydro-/vinylfluoroethers were prepared in a facile base-promoted addition using heteronucleophiles. • Regioselectivity of generated vinylfluoroethers was dependent on heteroatom of the nucleophile as demonstrated by nine examples. • Versatile synthetic methodology of this new class of fluorinated ethers synthesis should garner interest as useful intermediates for a multitude of materials applications. The nature of the structural configuration of fluorinated ethers has been widespread as a crucial component for improving high performance polymers, industrial agrochemicals, and targets for important pharmaceutical drugs. This is a result of countless advances in organo-fluorine methodologies with this unique substructure in order to overcome many traditional synthetic challenges. In this work, we expand on the preparation of fluorinated ethers by introducing hetero-nucleophiles to a highly electrophilic aryl trifluorovinyl ether affording a new class of difunctional aryl/alkyl fluorinated ethers that would serve as useful intermediates. The facile reaction chemistry of various nucleophile substrates, effect of base concerning regio-selectivity, and structural elucidation trends of the synthesized aryl/alkyl fluoroethers will be discussed. [Display omitted] [ABSTRACT FROM AUTHOR]