title: Access to 2'-substituted binaphthyl monoalcohols via complementary nickel-catalyzed Kumada coupling reactions under mild conditions: key role of a P,O ligand.
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.
authors.affiliation: Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078, United States.
authors.forename: Sachin
authors.initials: S
authors.lastname: Handa
authors.forename: Yohan L N
authors.initials: YL
authors.lastname: Mathota Arachchige
authors.forename: LeGrande M
authors.initials: LM
authors.lastname: Slaughter
mesh_terms: D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
chemical_list: C531594:(1,1'-binaphthalene)-2,2'-diol; D008024:Ligands; D009281:Naphthalenes; D009942:Organometallic Compounds; D010720:Phosphines; D009532:Nickel