Synthesis of carbazole-fused azaborines via a Pd-catalyzed C-H activation-cyclization reaction

Masakazu Nagata; Taku Oshiro; Yoshiyuki Mizuhata; Norihiro Tokitoh; Takaaki Hosoya; Shigeyuki Yamada; Tsutomu Konno; Hiroki Fukumoto; Toshio Kubota; Tomohiro Agou

doi:10.1246/BCSJ.20200129

Synthesis of carbazole-fused azaborines via a Pd-catalyzed C-H activation-cyclization reaction

Masakazu Nagata, Taku Oshiro, Yoshiyuki Mizuhata, Norihiro Tokitoh, Takaaki Hosoya, Shigeyuki Yamada, Tsutomu Konno, Hiroki Fukumoto, Toshio Kubota, Tomohiro Agou

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Carbazole-fused azaborines were synthesized via a Buchwald-Hartwig amination followed by a Pd-catalyzed C-H activation-cyclization reaction. These azaborines exhibited red-shifted absorptions and photoluminescence emissions compared to those of dibenzoazaborines, suggesting the efficient HOMO-LUMO energy gap decrease by the carbazole-annulation. The carbazole-fused azaborines showed improved electrochemical stability compared with the previously reported dibenzoazaborine derivatives.

Original language	English
Pages (from-to)	21-23
Number of pages	3
Journal	Bulletin of the Chemical Society of Japan
Volume	94
Issue number	1
DOIs	https://doi.org/10.1246/BCSJ.20200129
Publication status	Published - 2020
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry

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title = "Synthesis of carbazole-fused azaborines via a Pd-catalyzed C-H activation-cyclization reaction",

abstract = "Carbazole-fused azaborines were synthesized via a Buchwald-Hartwig amination followed by a Pd-catalyzed C-H activation-cyclization reaction. These azaborines exhibited red-shifted absorptions and photoluminescence emissions compared to those of dibenzoazaborines, suggesting the efficient HOMO-LUMO energy gap decrease by the carbazole-annulation. The carbazole-fused azaborines showed improved electrochemical stability compared with the previously reported dibenzoazaborine derivatives.",

author = "Masakazu Nagata and Taku Oshiro and Yoshiyuki Mizuhata and Norihiro Tokitoh and Takaaki Hosoya and Shigeyuki Yamada and Tsutomu Konno and Hiroki Fukumoto and Toshio Kubota and Tomohiro Agou",

note = "Publisher Copyright: {\textcopyright} 2021 The Chemical Society of Japan",

year = "2020",

doi = "10.1246/BCSJ.20200129",

language = "English",

volume = "94",

pages = "21--23",

journal = "Bulletin of the Chemical Society of Japan",

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T1 - Synthesis of carbazole-fused azaborines via a Pd-catalyzed C-H activation-cyclization reaction

AU - Nagata, Masakazu

AU - Oshiro, Taku

AU - Mizuhata, Yoshiyuki

AU - Tokitoh, Norihiro

AU - Hosoya, Takaaki

AU - Yamada, Shigeyuki

AU - Konno, Tsutomu

AU - Fukumoto, Hiroki

AU - Kubota, Toshio

AU - Agou, Tomohiro

PY - 2020

Y1 - 2020

N2 - Carbazole-fused azaborines were synthesized via a Buchwald-Hartwig amination followed by a Pd-catalyzed C-H activation-cyclization reaction. These azaborines exhibited red-shifted absorptions and photoluminescence emissions compared to those of dibenzoazaborines, suggesting the efficient HOMO-LUMO energy gap decrease by the carbazole-annulation. The carbazole-fused azaborines showed improved electrochemical stability compared with the previously reported dibenzoazaborine derivatives.

AB - Carbazole-fused azaborines were synthesized via a Buchwald-Hartwig amination followed by a Pd-catalyzed C-H activation-cyclization reaction. These azaborines exhibited red-shifted absorptions and photoluminescence emissions compared to those of dibenzoazaborines, suggesting the efficient HOMO-LUMO energy gap decrease by the carbazole-annulation. The carbazole-fused azaborines showed improved electrochemical stability compared with the previously reported dibenzoazaborine derivatives.

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DO - 10.1246/BCSJ.20200129

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JF - Bulletin of the Chemical Society of Japan

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ER -

Synthesis of carbazole-fused azaborines via a Pd-catalyzed C-H activation-cyclization reaction

Abstract

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