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

Abstract

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Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization Reactions

“…While the use of PhI(OAc) 2 , Hg(OAc) 2 , I 2 , or air, which were previously recommended for such purposes, [70] was unsuccessful in our hands leading either to no conversion or to a rapid degradation of the starting material, we were pleased to find that a combination of CuCl 2 ·2 H 2 O and tert-BuNH 2 in MeOH effected the desired oxidative coupling in satisfactory yields. [71] The spectral data of the somewhat sensitive 7,7'-bisaporphine derivative 75 match those reported in the literature. [60] Experimental Section [17] in CH 2 Cl 2 (40 mL) was slowly introduced and stirring was continued for 1 h at that temperature.…”

Synthesis, structure, and activity of (PhCH2NH2)2CuCl2 for oxidative coupling of 2‐naphthylamine

“…when CuCl 2 , benzylamine and 1 are used in a ratio of 2 : 8 : 1, compound 4 is isolated in 58% yield (Table 4, entry 3). 20,21,23 However, decreasing the ratio of amine to copper(II) leads to an increase in the isolated yield of 4 ( Table 4, entries 3-5), and the best conversion (73%, Table 4, entry 5) is obtained from a reaction condition of 2-naphthylamine (1), ethanolamine and CuCl 2 in ratio of 1 : 1 : 2. 26 This can be rationalized by a decreased solubility of the intermediate CuCl 2 -4 in the solution, when the amine concentration is reduced, and therefore favoring the complex CuCl 2 -4 formation.…”

CuBr/H2O2-Mediated Oxidative Coupling ofN,N-Dialkylarylamines in ­Water: A Practical Synthesis of Benzidine Derivatives

“…[15][16][17][18][19][20] In this broad context, copper(II) reagent was the mainly used oxidant for the coupling reaction of substrates with low oxidative potential, such as naphthols and naphthylamines. [21][22][23][24][25][26] Cu(I)-catalyzed aerobic oxidative coupling of 2-naphthol derivatives has also been reported. 27 However, in the case of oxidative coupling of aniline derivatives, all these copper reagents have never been involved, most probably due to their relatively lower oxidative activities.…”