使用 Selectfluor 进行氧化氟化：制备高价碘（V）氟化物的便捷程序。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-29 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.157

Samuel M G Dearman, Xiang Li, Yang Li, Kuldip Singh, Alison M Stuart

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引用次数: 0

摘要

研究高价碘（V）氟化物的能力一直受到限制，主要原因是传统上使用三氟甲基次萤石和三氟化溴等苛刻的氟化试剂很难制备高价碘（V）氟化物。在此，我们报告了一种使用 Selectfluor 制备高价碘（V）氟化物的温和而高效的方法，分离产率高（72-90%）。稳定性研究表明，双环二氟(芳基)-λ5-碘烷 6 在乙腈-d 3 中比在氯仿-d 1 中稳定得多，这可能是由于乙腈与碘(V)中心配位，并通过卤素键使其稳定。

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Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides.

The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72-90%). Stability studies revealed that bicyclic difluoro(aryl)-λ⁵-iodane 6 was much more stable in acetonitrile-d ₃ than in chloroform-d ₁, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.