Base-promoted nucleophilic fluoroarenes substitution of CF bonds. Issue 2 (11th January 2018)

• Record Type: Journal Article
• Authors: Su, Ji; Chen, Qian; Lu, Le; Ma, Yuan; Auyoung, George Hong Lok; Hua, Ruimao
• Is Part Of: Tetrahedron. Volume 74:Issue 2(2018)
• Page Start: 303
• Page End: 307
• Publication Date: 2018-01-11
• Subjects: Base-promoted -- Fluoroarenes -- Nucleophilic substitution -- C-F bond functionalization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.11.067
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for CF bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho -difluoroarenes and nucleophiles bearing ortho -dinucleophilic groups results in the formation of 2, 3-dihydro-1, 4-benzodioxins, dibenzo[b, e][1, 4]dioxins and 10 H -phenoxazines in moderate to good yields. Graphical abstract: