Construction of new quaternary carbon center of fluorinated isoxazolines at C5 position via C-F bond cleavage

IF 1.7 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Fluorine Chemistry Pub Date : 2024-08-30 DOI:10.1016/j.jfluchem.2024.110335

Kazuyuki Sato, Kazuki Nakano, Takahiro Ueda, Yukine Kitamura, Yuna Tanaka, Yukiko Karuo, Atsushi Tarui, Kentaro Kawai, Masaaki Omote

引用次数: 0

Abstract

A substitution reaction of O-, S-, or N-nucleophiles onto fluorinated isoxazolines via carbon–fluorine (C-F) bond cleavage was achieved. The C-F bond at the C5 position of fluorinated isoxazolines was dissociated by using SnCl₄ for the generation of a carbocation intermediate in this reaction. Subsequently, various nucleophiles such as alcohols, thiols, and amines were introduced, enabling the conversion to CO, C-S, or CN bonds and the formation of a new quaternary carbon center.

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通过 C-F 键裂解在 C5 位构建氟化异噁唑啉的新季碳中心

通过碳-氟（C-F）键裂解，实现了 O-、S-或 N-亲核物对氟化异恶唑啉的取代反应。在该反应中，通过使用 SnCl4 生成碳位中间体，离解了氟化异噁唑啉 C5 位上的 C-F 键。随后，引入醇、硫醇和胺等各种亲核剂，使其转化为 CO、C-S 或 CN 键，并形成新的季碳中心。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Fluorine Chemistry 化学-无机化学与核化学

CiteScore

3.80

自引率

10.50%

发文量

审稿时长

33 days

期刊介绍： The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.