Activation of tetrahydrofuran with 2-((Fluoroalkyl)thio)Benzothiazolium reagents. (19th November 2021)

• Record Type: Journal Article
• Authors: Maas, Lilian M.; Schmid, Jonas R.; Fasting, Carlo; Voßnacker, Patrick; Mavroskoufis, Andreas; Hopkinson, Matthew N.
• Is Part Of: Tetrahedron. Volume 101(2021)
• Publication Date: 2021-11-19
• Subjects: Benzothiazolium salts -- Organofluorine chemistry -- Ethers -- Ring opening reactions -- Lewis acid activation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132512
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The ability of BT-SCF3 and related 2-(fluoroalkylthio)benzothiazolium salts to activate tetrahydrofuran (THF) has been investigated. In the presence of carboxylate nucleophiles, ring-opening polymerization reactions affording various fluorinated and non-fluorinated polyethers are observed. Moreover, in the absence of a carboxylate, activation by the benzothiazolium allows for α-deprotonation of THF in the absence of a strong external base. In addition to these experimental studies, the Lewis acidity of BT-reagents is investigated by spectroscopic and quantum chemical methods. Graphical abstract: Image 1