Visible-light-induced photocatalytic iododi(per)fluoroalkylation of 5-amino-N-allyl-1,2,3-triazole-4-carboxamides

IF 1.7 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Fluorine Chemistry Pub Date : 2024-04-24 DOI:10.1016/j.jfluchem.2024.110292

Ivanna Yu. Danyliuk , Sergiy V. Kemskyi , Vladyslav M. Polishchuk , Svitlana V. Shishkina , Mykhailo V. Vovk

引用次数: 0

Abstract

Readily available di(per)fluoroalkyl iodides and ethyl difluoroiodoacetate have been efficiently reacted with 5-amino-N-allyl-1,2,3-triazole-4-carboxamides in the presence of DIPEA under visible-light induction and fluorescein catalysis to produce high yields of the corresponding adducts, N-(n-propyl) carboxamides vicinally difunctionalized with the iodine atom and the di(per)fluoroalkyl or (methoxycarbonyl)difluoromethyl moiety. As shown experimentally, this regiospecific and triazole amino group tolerant reaction involves a radical process.

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可见光诱导的 5-氨基-N-烯丙基-1,2,3-三唑-4-甲酰胺碘（过）氟烷基化光催化反应

在可见光诱导和荧光素催化下，现成的二（全）氟烷基碘化物和二氟碘乙酸乙酯与 5-氨基-N-烯丙基-1,2,3-三唑-4-甲酰胺在 DIPEA 存在下发生了高效反应，生成了高产率的相应加合物、N-（正丙基）羧酰胺与碘原子和二（全）氟烷基或（甲氧羰基）二氟甲基发生代双官能化反应。实验表明，这种具有区域特异性和三唑氨基耐受性的反应涉及一个自由基过程。

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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.