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

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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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2024-10-11
DOI
https://doi.org/10.3762/bjoc.20.216
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

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

Kohsuke Fujiwara, Akiya Ogawa, Yuki Yamamoto, Yuki Konakazawa
2 citations
Beilstein Journal of Organic Chemistry
Radical Photochemical Reactions
0.50
article

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

Kohsuke Fujiwara, Akiya Ogawa, Yuki Yamamoto, Yuki Konakazawa
article en
2 citations

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.

Beilstein Journal of Organic ChemistryVol. 20
Osaka Metropolitan University (JP), Takeda (Japan) (JP), University of Yamanashi (JP)
Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 39%
Radical Photochemical Reactions
0.50
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Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air — Kohsuke Fujiwara, Akiya Ogawa, et al. · Beilstein Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS