用三卤异氰尿酸和奥拉试剂进行炔烃的双卤代氟化反应

IF 1.7 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2023-11-01 DOI:10.1016/j.jfluchem.2023.110214

Hugo da S. Bragueroli, Pierre M. Esteves, Marcio C.S. de Mattos

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引用次数: 0

摘要

介绍了以三卤异氰尿酸为卤化剂，吡啶(HF) X (Olah试剂)为氟源，通过炔烃双卤代氟化反应生成与CX2 (X =氯或溴)相邻的CF2基团的简单高效方法。所使用的炔有1-己炔、3-己炔、苯乙炔、1-苯基-1-丁炔和二苯乙炔，产率主要在30 - 88%。在所研究的三卤异氰尿酸中，三溴异氰尿酸产率最好，反应选择性最强，而三氯异氰尿酸虽然反应性最强，但在所研究的反应中选择性较低，有时会产生几种副产物。

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The double halofluorination reaction of alkynes using trihaloisocyanuric acids and Olah's reagent

A simple and efficient method to produce a CF₂ group vicinal to a CX₂ group (X = chlorine or bromine) through double halofluorination reaction of alkynes using trihaloisocyanuric acid as halogenating agent and Pyridine.(HF)_x (Olah's reagent) as fluoride source is presented. The alkynes used were 1-hexyne, 3-hexyne, phenylacetylene, 1-phenyl-1-butyne, and diphenylacetylene, obtaining, mainly, the desired products in 30–88 % yields. Among the trihaloisocyanuric acids studied, the tribromoisocyanuric acid gave the best yields and the most selective reactions, while trichloroisocyanuric acid, although the most reactive, had less selectivity in the reactions studied, giving in some cases several by-products.

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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.