Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C–N coupling and C–H activation reactions

Hung, Tran Quang; Thang, Ngo Ngoc; Hoang, Dinh Thai; Dang, Tuan Thanh; Villinger, Alexander; Langer, Peter

doi:10.1039/c3ob41746h

Cited by 29 publications

(10 citation statements)

References 25 publications

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“…More recently, Dang, Langer, and their co-workers reported a multistep route to biscarbazoles 148a and 148b ( Scheme 29 , next page) involving three Pd-catalyzed coupling reactions of anilines. 134 First, inter- and intramolecular N-arylation of p -anisidines (top) or m -anisidines (bottom) with bistriflate 146 furnished carbazoles 147a and 147b . Subsequent conversion of the methoxy groups into triflates, followed by an N-arylation/C–H activation sequence, successfully introduced a second carbazole into the structure, yielding 3,9′- and 2,9′-biscarbazoles ( 148a and 148b ).…”

Section: Anilinesmentioning

confidence: 99%

“… In the presence of L26 , a variety of primary anilines and several alkylamines were successfully coupled with 2,2′-dihalobiphenyls to provide the desired N-substituted carbazoles ( 145 ) in 34–99% yield. More recently, Dang, Langer, and their co-workers reported a multistep route to biscarbazoles 148a and 148b (Scheme , next page) involving three Pd-catalyzed coupling reactions of anilines . First, inter- and intramolecular N-arylation of p -anisidines (top) or m -anisidines (bottom) with bistriflate 146 furnished carbazoles 147a and 147b .…”

Section: Anilinesmentioning

confidence: 99%

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Anilinesmentioning

confidence: 99%

Section: Anilinesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…Regarding the catalytic use of metallic nanoparticles, in particular those of palladium and copper, as a current strategy in organic synthesis in virtue of their wide scope of chemical reactions compared to homogeneous catalytic systems, in this review, the state of the art on the preparation of fine chemicals from multi-step transformations from a sustainable point of view is analyzed [ 7 , 8 , 9 , 10 , 11 , 12 ]. During the last decade, a prominent review was reported by Buchwald et al (2016) regarding homogeneous palladium-catalyzed multi-step transformations, mainly in C–N cross-coupling reactions [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

et al. 2021

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Metal nanoparticles have been deeply studied in the last few decades due to their attractive physical and chemical properties, finding a wide range of applications in several fields. Among them, well-defined nano-structures can combine the main advantages of heterogeneous and homogenous catalysts. Especially, catalyzed multi-step processes for the production of added-value chemicals represent straightforward synthetic methodologies, including tandem and sequential reactions that avoid the purification of intermediate compounds. In particular, palladium- and copper-based nanocatalysts are often applied, becoming a current strategy in the sustainable synthesis of fine chemicals. The rational tailoring of nanosized materials involving both those immobilized on solid supports and liquid phases and their applications in organic synthesis are herein reviewed.

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“…Bicarbazole (BCz) derivatives could further increase the structural diversity of the Cz framework through multifarious ways of linking two Cz units. Chemically speaking, BCz derivatives include 15 isomers (Figure ), namely, 1,1′‐, 1,2′‐,, 1,3′‐,, 1,4′‐,, 2,2′‐, 2,3′‐, 2,4′‐, 3,3′‐, 3,4′‐, 4,4′‐,, 1,9′‐, 2,9′‐, 3,9′‐, 4,9′‐, and 9,9′‐BCz . Although many BCz derivatives have been prepared and used as OLED materials,–– a large number of new materials based on BCz demonstrate great potential for OLED applications.…”

Section: Introductionmentioning

confidence: 99%

9,9′‐Bicarbazole: New Molecular Skeleton for Organic Light‐Emitting Diodes

Liu

Zhang

Fei

et al. 2019

Chemistry A European J

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Carbazole is a classic tricyclic aromatic compound that has been widely used in organic optoelectronics. Appropriate functionalization on its aromatic rings will significantly increase the possibilities for its application as an optoelectronic material. Position engineering of carbazole not only leads to its structural diversity, but also substantially enriches its functionality. Bicarbazoles have 15 isomers, most of which are well studied and have been applied in organic light‐emitting diodes (OLEDs). However, one isomer, 9,9′‐bicarbazole, is rarely investigated as an OLED material. Therefore, two 9,9′‐bicarbazole derivatives, 3,3′‐di(10H‐phenoxazin‐10‐yl)‐9,9′‐bicarbazole and 3,3′‐di(10H‐phenothiazin‐10‐yl)‐9,9′‐bicarbazole, have been designed and prepared for use as host materials for green and red OLEDs. These two compounds demonstrated good device performances, and it is believed that the 9,9′‐bicarbazole building block could be a novel platform for the design of efficient host materials for OLEDs.

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Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C–N coupling and C–H activation reactions

Cited by 29 publications

References 25 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

9,9′‐Bicarbazole: New Molecular Skeleton for Organic Light‐Emitting Diodes

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