Access to 2′-Substituted Binaphthyl Monoalcohols via Complementary Nickel-Catalyzed Kumada Coupling Reactions under Mild Conditions: Key Role of a P,O Ligand
The Journal of Organic Chemistry2013Vol. 78(11), pp. 5694–5699
Citations Over TimeTop 18% of 2013 papers
Abstract
Two complementary Kumada coupling methods for the conversion of monotriflated 1,1'-binaphthalene-2,2'-diol (BINOL) into 2'-substituted binaphthyl monoalcohols under mild conditions are reported. A protocol using NiCl2(dppe), in combination with an improved preparation of the monotriflate, is effective for 1,1'-binaphthalene-2-ols containing unsubstituted or electron-poor aryl or benzyl 2'-substituents. An alternative procedure, using a potentially hemilabile-bidentate phosphinan-4-ol ligand, is superior for products containing neopentyl or electron-rich aryl 2'-substituents. The obtained binaphthyl alcohols represent potentially useful synthons for chiral ligands and auxiliaries.
Related Papers
- → Nickel release from coins(2001)100 cited
- → Diazadien-Nickel-Komplexe, I: Bis(diazadien)-nickel(O) und Bromo-diazadien-nickel(I) / Diazadiene Nickel Complexes, I: Bis(diazadiene) Nickel(O) and Bromo-diazadiene Nickel(I)(1978)50 cited
- → Effects of nickel source material on characteristics of nickel/alumina impregnated catalysts.(1987)5 cited
- → (1979)1 cited
- → ChemInform Abstract: Trivalent Nickel Bis(triaza macrocyclic) Complexes. Ligand Ring Size and Medium Effects on the Nickel(III)/Nickel(II) Redox Couple Potential.(1986)