57103-14-7

Upstream product

• 13029-09-9 2,2'-dibromobiphenyl 
• 371-40-4 4-fluoroaniline 
• 13029-08-8 2,2'-Dichlorobiphenyl 
• 1454610-64-0 dibenzo[b,d]bromol-5-ium trifluoromethanesulfonate 
• 2113-51-1 2-iodobiphenyl 
• 54147-91-0 2’-bromo-[1,1’-biphenyl]-2-amine 
• 615-43-0 2-iodophenylamine 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 98-80-6 phenylboronic acid 
• 609-73-4 o-nitroiodobenzene 
• 86-00-0 2-nitrobiphenyl 
• 1016-05-3 dibenzothiophene sulfone 
• 2052-07-5 2-Bromobiphenyl 
• 3296-02-4 p-azidofluorobenzene 

Downstream Products

• 922721-30-0 3-bromo-9-(p-fluorophenyl)-9H-carbazole 
• 922721-29-7 (carbazole-diyl)(pyridyl)(C₆H₄F) 
• 1222558-52-2 3,6-diiodo-9-(4-fluoro-phenyl)-9H-carbazole 
• 1039761-06-2 C₁₈H₁₃BFNO₂ 
• 1246261-65-3 4,4'-bis(9-(p-fluorophenyl)-9H-carbazol-3-yl)-1,1'-binaphthyl 
• 1385028-98-7 C₄₁H₂₅F₂N₃ 
• 934704-43-5 (4-(9H-carbazol-9-yl)phenyl)diphenylphosphine oxide 

Relevant academic research and scientific papers

Method for synthesizing carbazole derivative

The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

Palladium-catalyzed C-H bond activation for the assembly of: N -aryl carbazoles with aromatic amines as nitrogen sources

A convenient and efficient palladium-catalyzed C-H bond activation for the assembly of N-aryl carbazole is reported, in which two C-N bonds were formed under one set of conditions. The desired carbazoles were achieved in decent yields with a wide substrate scope by utilizing readily available 2-iodo biphenyls and aromatic amines as starting materials.

Design, synthesis and biological evaluation of: N -arylsulfonyl carbazoles as novel anticancer agents

In this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure-activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase. Finally, the in vivo study demonstrated that 8h prevented the tumor growth in PANC-1 and Capan-2 xenograft models without apparent toxicity.

Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide

A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.

Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes

A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.

Photochemical Synthesis of Carbazoles Using an [Fe(phen)3](NTf2)2/O2 Catalyst System: Catalysis toward Sustainability

An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)3(NTf2)2/O2 under continuous flow conditions and was demonstrated on gram-scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.

A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides

The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.

Copper/β-diketone-catalysed N-arylation of carbazoles

A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.

Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow

An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.