Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent. Issue 8 (14th January 2021)

• Record Type: Journal Article
• Authors: Kalim, Jorna; Duhail, Thibaut; Pietrasiak, Ewa; Anselmi, Elsa; Magnier, Emmanuel; Togni, Antonio
• Is Part Of: Chemistry. Volume 27:Issue 8(2021)
• Page Start: 2638
• Page End: 2642
• Publication Date: 2021-01-14
• Subjects: hypervalent iodine -- organofluorine compounds -- sulfoximines -- trifluoromethylation -- trifluoromethylethers; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202005104
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The direct trifluoromethylation of a variety of aliphatic alcohols using a hypervalent iodosulfoximine reagent afforded the corresponding ethers in moderate to good yields (14–72 %). Primary, secondary, and even tertiary alcohols, including examples derived from natural products, underwent this transformation in the presence of catalytic amounts of zinc bis(triflimide). Typical reaction conditions involved a neat mixture of 6.0 equivalents of the alcohol with 1.0 equivalent of the reagent, with the majority of reactions complete within 2 h with 2.5 mol % of the Lewis acid catalyst. Furthermore, experimental evidence was provided that the C−O bond‐forming process occurred via the coordination of the alcohol to the iodine atom and subsequent reductive elimination. Abstract : Trilfuoromethylethers made easy ! An operationally simple method using the new hypervalent iodosulfoximine reagent alongside minimal amounts of a zinc catalyst gives access to a variety of different trifluoromethylethers, in under 2 h for most cases.