Synthesis of Solubility-Enhanced 6,8-Diarylated Dibromodibenzo[a,j]Phenazines via Pd-Catalyzed C─H Arylation and Skeletal Rearrangement

Namba, Naohiro; Tohnai, Norimitsu; Minakata, Satoshi et al.

Asian Journal of Organic Chemistry, 2025, e70211

アクセス数:21件（2025-12-05 16:23 集計）

固定URL: https://hdl.handle.net/11094/102987

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タイトル
Synthesis of Solubility-Enhanced 6,8-Diarylated Dibromodibenzo[a,j]Phenazines via Pd-Catalyzed C─H Arylation and Skeletal Rearrangement
著者
著者名
Namba, Naohiro
NRID
1000030346184 1000030346184
ORCID
0000-0001-7051-7599 0000-0001-7051-7599
researchmap permalink
read0089607 read0089607
Scopus Author ID
6701482198 6701482198
著者名
Tohnai, Norimitsu
NRID
1000090273599 1000090273599
ORCID
0000-0001-9619-445X 0000-0001-9619-445X
researchmap permalink
read0185263 read0185263
Scopus Author ID
7003640913 7003640913
著者名
Minakata, Satoshi
NRID
1000060608785 1000060608785
ORCID
0000-0001-9103-4238 0000-0001-9103-4238
researchmap permalink
read0156438 read0156438
Scopus Author ID
12753487600 12753487600
著者名
Takeda, Youhei
キーワード等
Building blocks
Phenazines
Skeletal rearrangement
Solubility; π-conjugated molecules
内容
Namba N., Tohnai N., Minakata S., et al. Synthesis of Solubility-Enhanced 6,8-Diarylated Dibromodibenzo[a,j]Phenazines via Pd-Catalyzed C─H Arylation and Skeletal Rearrangement. Asian Journal of Organic Chemistry , (2025); https://doi.org/10.1002/ajoc.70211.
抄録
We report the synthesis of a new class of dibromodibenzo[a,j]phenazine (DBPHZ) derivatives bearing diaryl substituents at the 6,8–positions. These compounds were obtained through a combination of regioselective Pd-catalyzed C─H direct arylation and oxidative skeletal rearrangement of appropriately functionalized binaphthalenediamines. The compatibility of bromine substituents with the C─H arylation conditions was confirmed, enabling the incorporation of various aryl groups including diphenyl, tert-butylphenyl, and 3,5-dimethylphenyl moieties. Crystallographic analysis of a representative compound revealed that the diaryl units adopt a twisted geometry relative to the DBPHZ core. Solubility tests demonstrated that the introduction of diaryl substituents having alkyl groups significantly enhances solubility in common organic solvents such as toluene and chloroform, compared to unsubstituted DBPHZ. Owing to the retained dibromo functionality, the synthesized DBPHZs would serve as valuable synthetic building blocks for constructing π-extended functional organic materials.
出版者
John Wiley and Sons Inc
収録物名
Asian Journal of Organic Chemistry
ページ
e70211
刊行年月
2025-09-23
言語
英語
ハンドルURL
https://hdl.handle.net/11094/102987
eISSN
21935815
関連情報 (isIdenticalTo)
DOI (出版社版)
https://doi.org/10.1002/ajoc.70211
アクセス権
open access
権利情報
This article is licensed under a Creative Commons Attribution 4.0 International License.
出版タイプ
Version of Record
カテゴリ
学術雑誌論文 Journal Article