Dialkylzinc-mediated allylic polyfluoroarylation reaction. Issue 35 (2nd September 2015)

• Record Type: Journal Article
• Authors: Kurauchi, Daisuke; Hirano, Keiichi; Kato, Hisano; Saito, Tatsuo; Miyamoto, Kazunori; Uchiyama, Masanobu
• Is Part Of: Tetrahedron. Volume 71:Issue 35(2015)
• Page Start: 5849
• Page End: 5857
• Publication Date: 2015-09-02
• Subjects: Polyfluoroarylation -- Allylic substitution -- Halogen–zinc exchange -- Chemoselective; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.05.107
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We present an allylic polyfluoroarylation reaction with broad substrate scope and excellent functional group tolerance, using organozinc reagents under mild conditions. A catalytic amount of triphenylphosphine oxide efficiently promotes iodine–zinc exchange reaction between polyfluoroaryl iodide and dimethylzinc, and the resulting phosphine oxide-activated polyfluoroarylzinc undergoes substitution reaction with allylic halides to afford the corresponding polyfluoroarylated products. Graphical abstract: