Synthesis of Aryl‐ and Heteroaryl‐Trifluoroethyl Ethers: Aims, Challenges and New Methodologies

Abstract

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Fluorination and Fluoroalkylation Reactions Mediated by Hypervalent Iodine Reagents

“…The importance of fluoroalkylether function in the field of medicinal chemistry has been demonstrated by a large number of the well-known bioactive aryl-or heteroaryl-fluoroalkyl ethers, e. g., flecainide, silodosin, and lansoprazole. [91] The applicability of trifluoroethoxy group as a protected phenolic OH moiety in the total synthesis is also evidenced. [91] Considering the usefulness of fluoroalkylethers, it is reasonable that many efforts have been made for the synthesis of these compounds.…”

“…[91] The applicability of trifluoroethoxy group as a protected phenolic OH moiety in the total synthesis is also evidenced. [91] Considering the usefulness of fluoroalkylethers, it is reasonable that many efforts have been made for the synthesis of these compounds. The introduction of fluoroalkoxy groups into aromatic systems is a challenging task.…”

“…The introduction of fluoroalkoxy groups into aromatic systems is a challenging task. Two major retrosynthetic paths have been devised for preparing aryl fluoroalkyl ethers . In one approach, C−O bond formation occurs between a OH species and a fluoroalkyl electrophile synthon, while in the other option the C−O bonds are constructed by the reactions of fluoroalkoxy synthons with aryl or other species.…”

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes

“…Synthetic methodologies for the construction of alkyl or aryl ethers are well established with metal‐free [44] or metal‐based procedures [45] providing easy access to these moieties. In comparison, heteroaryl ethers have found utility in the pharmaceutical and agricultural sectors and their importance is growing at a rapid rate [46] . However, the synthetic routes available for the construction of these molecules, especially the metal‐catalyzed versions have several inadequacies including lower yields, higher concentration of the added catalyst as well as a high reaction temperature [47] .…”

“…In comparison, heteroaryl ethers have found utility in the pharmaceutical and agricultural sectors and their importance is growing at a rapid rate. [46] However, the synthetic routes available for the construction of these molecules, especially the metal-catalyzed versions have several inadequacies including lower yields, higher concentration of the added catalyst as well as a high reaction temperature. [47] The state-of-the-art in terms of catalytic etherification of arenes as well as heteroarenesis mainly associated with the Buchwald group [48] (RockPhos used as ligand), while the Hierso [49] group has also been actively involved in this area with its ferrocenyl phosphine ligands.…”