128702-23-8Relevant academic research and scientific papers
Synthesis of (±) binaphthols via oxidative coupling of naphthols by cerium ammonium nitrate (CAN)
Jiang,Lu
, p. 131 - 134 (2001)
2-Naphthol and methyl 3-hydroxy-2-naphthoate were oxidized to give the corresponding (±) binaphthols by cerium ammonium nitrate (CAN) in good yields.
Lewis acid-assisted oxidative cross-coupling of 2-naphthol derivatives with copper catalysts
Yan, Pei,Sugiyama, Yukihiro,Takahashi, Yusuke,Kinemuchi, Haruki,Temma, Tomohisa,Habaue, Shigeki
, p. 4325 - 4331 (2008)
The oxidative coupling reactions between 2-naphthol and 3-hydroxy-2-naphthoic acid derivatives using a copper catalyst under an O2 atmosphere in the presence of a catalytic amount of the Lewis acid, such as Yb(OTf)3, were carried out. A highly cross-coupling selective or specific reaction effectively proceeded to give a C1 symmetrical BINOL derivative.
The oxidative cross-coupling of substituted 2-naphthols. Part II: Sensitivity as a mechanistic probe
Hovorka,Zavada
, p. 9517 - 9530 (1992)
Mechanistic study of Cu(II)-mediated coupling revealed that the model reaction between 2-naphthol and 3-carbomethoxy 2-naphthol can be controlled to give either the cross-coupled product (4) or a non-selective/approximately 1:1/mixture of the cross- and homo-coupled products (4) and (5), respectively, the alternative homo-product (3) being virtually absent in both instances. The copper/ligand ratio has been found to be the main controlling factor and operation of two active copper species differing greatly in selectivity as well as reactivity has been suggested. Plausible model of a binuclear Cu(II) complex explaining the preferential cross-coupling has been devised and possible relevance to the oxidative polymerization of 2,6-dimethylphenol has been considered.
Ytterbium triflate-assisted catalytic oxidative cross-coupling of 2-naphthol derivatives
Habaue, Shigeki,Temma, Tomohisa,Sugiyama, Yukihiro,Yan, Pei
, p. 8595 - 8598 (2008/03/30)
The oxidative coupling of 2-naphthol and 3-hydroxy-2-naphthoate derivatives with a copper catalyst under an O2 atmosphere was carried out. The reaction in the presence of a catalytic amount of the Lewis acid, Yb(OTf)3, proceeded in a cross-coupling specific manner.
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
Smrcina, Martin,Vyskocil, Stepan,Maca, Bohumil,Polasek, Miroslav,Claxton, Thomas A.,et al.
, p. 2156 - 2163 (2007/10/02)
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.
The oxidative cross-coupling of substituted 2-naphthols. Part I: The scope and limitations
Hovorka,Scigel,Gunterova,Tichy,Zavada
, p. 9503 - 9516 (2007/10/02)
Highly selective oxidative cross-coupling of differently substituted 2-naphthols mediated by Cu(II)-tert-butyl amine complexes is described. The 'cross'-products are obtained in good to excellent yields and the selectivity up to >90% is observed depending on the substitution of naphthol nuclei. The alternative procedures - the cross-coupling of free naphthols with CuCl(OMe) as well as the coupling of sodium naphtholates with anhydrous copper(II) chloride - were also studied. All these methods enable a simple and high-yield access to the unsymmetrically substituted binaphthols. A successful optical resolution of methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate by means of liquid chromatography on triacetylcellulose and the subsequent configurational correlation with a binaphthol derivative of known absolute configuration is reported.
HIGHLY SELECTIVE OXIDATIVE CROSS-COUPLING OF SUBSTITUTED 2-NAPHTHOLS: A CONVIENT APPROACH TO UNSYMMETRICAL 1,1'-BINAPHTHALENE-2,2'-DIOLS
Hovorka, Martin,Guenterova, Jana,Zavada, Jiri
, p. 413 - 416 (2007/10/02)
Oxidative cross-coupling of several differently substituted 2-naphthols mediated by Cu(II)-amine complexes is described.The influence of substituents was examined and possible mechanism explaining the observed selectivity has been proposed.
