Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[<i>c, g</i>]carbazoles

Abstract A Cu(II) complex with a bipyridyl ligand bearing a Brønsted acid was used to catalyze the tandem oxidative coupling and cyclization of 2‐aminonaphthalenes to give N ‐substituted‐dibenzo[ c,g ]carbazoles. The incorporation of an appended acidic moiety to the ligand was found to be key to the selective formation of dibenzocarbazoles over 2,2’‐diamino‐1,1’‐binaphthalene (BINAM), which is known as an irreversible byproduct. This highly efficient method yields a wide array of dibenzo[ c,g ]carbazoles featuring diverse functional groups as well as electronic properties. The selected dibenzo[ c,g ]carbazoles exhibited high photoluminescence quantum yields of up to 100 % and are promising chromophores for advanced materials.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-10-25
DOI
https://doi.org/10.1002/ajoc.202400366
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.50

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article

Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[c, g]carbazoles

Arnab Ghosh, Houng Kang, Myung Hwan Park, Min Kim et al.
2 citations
Asian Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.50
article

Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[c, g]carbazoles

Arnab Ghosh, Houng Kang, Myung Hwan Park, Min Kim, M. S. KONG
article en
2 citations

Abstract

Abstract A Cu(II) complex with a bipyridyl ligand bearing a Brønsted acid was used to catalyze the tandem oxidative coupling and cyclization of 2‐aminonaphthalenes to give N ‐substituted‐dibenzo[ c,g ]carbazoles. The incorporation of an appended acidic moiety to the ligand was found to be key to the selective formation of dibenzocarbazoles over 2,2’‐diamino‐1,1’‐binaphthalene (BINAM), which is known as an irreversible byproduct. This highly efficient method yields a wide array of dibenzo[ c,g ]carbazoles featuring diverse functional groups as well as electronic properties. The selected dibenzo[ c,g ]carbazoles exhibited high photoluminescence quantum yields of up to 100 % and are promising chromophores for advanced materials.

Asian Journal of Organic ChemistryVol. 14(1)
Chungbuk National University (KR), Seowon University (KR)
National Research Foundation, Chungbuk National University, National Research Foundation of Korea, Ministry of Science and ICT, South Korea
Openalex Percentile: Top 38%
Catalytic C–H Functionalization Methods
0.50
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