Expeditious Access to the B 3 NO 2 Heterocycle Enabling Modular Derivatization

Expeditious Access to the B 3 NO 2 Heterocycle Enabling Modular Derivatization

DATB (1,3-dioxa-5-aza-2,4,6-triborinane) is a unique six-membered heterocycle exhibiting proficient catalytic activity in direct dehydrative amidation. Reported herein is an improved synthetic protocol for DATB derivatives featuring a concise two-step chromatography-free process. Suzuki-Miyaura coup...

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Veröffentlicht in:Journal of organic chemistry 2023-05, Vol.88 (9), p.6247-6251
Hauptverfasser: Tsutsumi, Ryosuke, Kashiwagi, Nobuaki, Kumagai, Naoya
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container_end_page 6251
container_issue 9
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container_title Journal of organic chemistry
container_volume 88
creator Tsutsumi, Ryosuke
Kashiwagi, Nobuaki
Kumagai, Naoya
description DATB (1,3-dioxa-5-aza-2,4,6-triborinane) is a unique six-membered heterocycle exhibiting proficient catalytic activity in direct dehydrative amidation. Reported herein is an improved synthetic protocol for DATB derivatives featuring a concise two-step chromatography-free process. Suzuki-Miyaura coupling assembled 2,6-dibromoaniline derivatives and 1,2-phenylenediboronic acid to afford dimeric -spiroborate salts. Acidic untying of the spiroborates gave rise to the DATB ring system with various substituents.
doi_str_mv 10.1021/acs.joc.3c00426
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title Expeditious Access to the B 3 NO 2 Heterocycle Enabling Modular Derivatization
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