Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-10-11 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.216
Yuki Yamamoto, Yuki Konakazawa, Kohsuke Fujiwara, Akiya Ogawa
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Abstract

A simple and versatile synthesis of arylboronates has been achieved by using triarylbismuthines as aryl radical sources under transition-metal-free and open-air conditions. Conventional methods required photoirradiation or electrolysis to generate aryl radicals from triarylbismuthines. In this study, it was found that simply heating the solution of triarylbismuthines in benzotrifluoride (BTF) in air successfully led to the generation of aryl radicals, and the subsequent reaction with bis(pinacolato)diboron afforded a variety of arylboronates in moderate to good yields.

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在空气中通过热力从三芳基铋生成芳基自由基的无过渡金属芳基硼酸盐合成。
在无过渡金属和露天条件下,利用三芳基铋作为芳基自由基源,实现了芳基硼酸盐的简单和多功能合成。传统方法需要光照射或电解才能从三芳基铋中生成芳基自由基。本研究发现,只需在空气中加热三芳基铋在三氟甲苯(BTF)中的溶液,就能成功生成芳基自由基,随后与双(频哪甲酰基)二硼发生反应,就能以中等至良好的收率得到各种芳基硼酸盐。
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来源期刊
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.
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