Copper‐Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a CCF3 Bond from an O‐Based Electrophile. Issue 38 (6th August 2013)

• Record Type: Journal Article
• Authors: Zhu, Lingui; Liu, Shasha; Douglas, Justin T.; Altman, Ryan A.
• Is Part Of: Chemistry. Volume 19:Issue 38(2013)
• Page Start: 12800
• Page End: 12805
• Publication Date: 2013-08-06
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302328
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The conversion of an alcohol‐based functional group, into a trifluoromethyl analogue is a desirable transformation. However, few methods are capable of converting O‐based electrophiles into trifluoromethanes. The copper‐mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF₃ to form CCF₃ bonds is described. The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the CCF₃ bond forms by reaction of the substrate with in situ generated CuCF₃ and CuOTf. Further evidence suggests that the reaction could proceed via a radical cation intermediate.</p> </abstract>