21720-66-1

Upstream product

• 135-88-6 N-Phenyl-2-naphthylamine 
• 62-53-3 aniline 
• 602-09-5 1,1'-bi-2-naphthol 
• 71-43-2 benzene 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 27067-31-8 N-phenyl 2-naphthyl nitroxide 
• 7647-01-0 hydrogenchloride 
• 17704-02-8 N,N'-diphenyl-(1,1'-binaphthyl)-2,2'-diamine 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 

Relevant academic research and scientific papers

An intermolecular C-H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines

Highly π-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies. Therefore, developing efficient, pre-activation-free, synthetic procedures for the rapid build-up of these complex structures remains a high priority objective. The herein presented approach delivers highly fused carbazole skeletons from simple naphthylamine derivatives.

Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions

A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.

Copper(II)-mediated oxidative coupling of 2-aminonaphthalene homologues. Competition between the straight dimerization and the formation of carbazoles

Whereas the Cu(II)-mediated oxidative coupling of 2-aminonaphthalenes 7a and 7b results in the clean formation of 1,1′-binaphthyls 13a and 13b, respectively, their higher homologues and congeners 8 - 12 have been found to exhibit a different reaction pattern. Thus, 2-aminoanthracene (8) gave a ～1:1 mixture of the expected bianthryl derivative 15 and the carbazole 16, whereas the 9-aminophenanthrene (10), 3-phenyl-1-aminonaphthalene (11), and 2-aminochrysene (12) produced almost exclusively the corresponding carbazoles 19, 20, and 21, respectively. By contrast, the isomeric 3-aminophenanthrene (9) gave rise to the azo compound 17 as a result of the preferential oxidation on the nitrogen. The carbazoles have been shown to arise directly from the coupling reactions rather than from the primarily formed binaphthyls. Alternatively, carbazole 19 can also be prepared from 1b on reaction with hydrazine. On the other hand, treatment of 3a with hydrazine resulted in the formation of a ～2:7 mixture of amine 11 and arylhydrazine 22. 2,2′-Diamino-1,1′-bianthryl (15) has been resolved into enantiomers via Cocrystallization with (-)-N-benzylcinchonidinium chloride and shown to have (R)-(-)-15 configuration by X-ray crystallography.

Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls

The novel 1,1'-binaphthyls with OH and/or NHR (R = H or Ph) groups in the 2,2'-positions and with additional methoxycarbonyl group(s) in the 3- or 3,3'-positions (13-18) have been synthesized from their respective precursors 1-5 by the CuCl2/t-BuNH2-mediated oxidative cross-coupling.In most cases, the chemoselectivity was good, and the cross-coupled products 11-18 were obtained in fair to excellent yields.Binaphthyls 6-10, resulting from the selfcoupling, and carbazoles 19-23 have been identified as byproducts.Ab initio calculations and electrochemical measurements have been employed to account for the observrd selectivity.

Nitroxide Radicals. Part 21. Spontaneous Decomposition of N-Aryl 1- and 2-Naphthyl Nitroxides

N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines.When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced.N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.