Version 1
: Received: 23 July 2024 / Approved: 23 July 2024 / Online: 23 July 2024 (13:51:23 CEST)
How to cite:
Kawaguchi, H.; Fuse, K.; Maeda, N.; Kuwabara, T. Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole. Preprints2024, 2024071789. https://doi.org/10.20944/preprints202407.1789.v1
Kawaguchi, H.; Fuse, K.; Maeda, N.; Kuwabara, T. Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole. Preprints 2024, 2024071789. https://doi.org/10.20944/preprints202407.1789.v1
Kawaguchi, H.; Fuse, K.; Maeda, N.; Kuwabara, T. Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole. Preprints2024, 2024071789. https://doi.org/10.20944/preprints202407.1789.v1
APA Style
Kawaguchi, H., Fuse, K., Maeda, N., & Kuwabara, T. (2024). Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole. Preprints. https://doi.org/10.20944/preprints202407.1789.v1
Chicago/Turabian Style
Kawaguchi, H., Nanoka Maeda and Takuya Kuwabara. 2024 "Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole" Preprints. https://doi.org/10.20944/preprints202407.1789.v1
Abstract
The general synthesis of boron-containing cyclic compounds (boracycles) necessitates toxic organotin precursors or highly reactive boron halides. Here we report the synthesis of seven- and five-membered boracycles utilizing arylboronic acid pinacol esters (ArBpins) as stable boron sources. Grignard reagents generated from 2,2′-dibromodibenzyl or 2,2′-dibromobiphenyl reacted with ArBpins, where Ar = 9-anthryl (Anth), 2,4,6-trimethylphenyl (Mes), 2,4,6-triisopropylphenyl (Tip), to give 10,11-dihydro-5H-dibenzo[b,f]borepins or dibenzoborole derivatives. This Bpin-based method was successfully applied to a one-shot double boracycle formation, providing a dihydrodibenzoborepin–anthracene–dihydrodibenzoborepin triad molecule in a good yield. The dihydrodibenzoborepin bearing the Anth group was directly converted to the unsaturated borepin by NBS/AIBN. All products were characterized by NMR, HRMS, and in some cases, single-crystal X-ray diffraction analysis. Additionally, the photophysical properties of the products are also reported.
Chemistry and Materials Science, Organic Chemistry
Copyright:
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