Ring-opening fluorination of cyclopropylmethanols and cycloprpanecarbardehydes with diethylaminosulfur trifluoride. (2nd February 2021)

• Record Type: Journal Article
• Authors: Kirihara, Masayuki; Kikkawa, You; Nakamura, Riho; Nakakura, Kana; Suzuki, Yasuhiro; Muramatsu, Yukari
• Is Part Of: Tetrahedron letters. Volume 64(2021)
• Publication Date: 2021-02-02
• Subjects: Ring-opening fluorination -- Cyclopropane -- DAST -- Homoallylic fluoride -- 1, 4-Difluorination; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152655
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Arylated cyclopropylmethanols react with DAST to produce homoallylic fluorides. Arylated cyclopropanecarbaldehydes reacts with DAST to produce 1, 4-difluorobut-1-enes. The reaction proceeds via a carbocation intermediate. Abstract: The reaction of cyclopropylmethanols bearing aromatic substituents on their cyclopropane rings with diethylaminosulfur trifluoride (DAST) effectively caused ring-opening fluorination to produce homoallylic fluorides. This reaction proceeded via a carbocation intermediate. DAST reacted with cyclopropanecarbaldehydes having electron donating aromatic substituents to cause ring-opening fluorinations with the addition of two fluorine atoms to afford 1, 4-difluorobut-1-enes.