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Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols.
Molecules. 2020 Feb 14; 25(4)M

Abstract

An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1'-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)-N1,N2-di(quinolin-8-yl)cyclohexane-1,2-diamine, L1]. A number of ligands (L2-L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

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Authors+Show Affiliations

Wu LY
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.
Usman M
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.
Liu WB
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.

MeSH

CatalysisIronLigandsMolecular StructureNaphtholsOxidation-ReductionOxidative CouplingStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32075144

Citation

Wu, Lin-Yang, et al. "Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols." Molecules (Basel, Switzerland), vol. 25, no. 4, 2020.
Wu LY, Usman M, Liu WB. Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols. Molecules. 2020;25(4).
Wu, L. Y., Usman, M., & Liu, W. B. (2020). Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols. Molecules (Basel, Switzerland), 25(4). https://doi.org/10.3390/molecules25040852
Wu LY, Usman M, Liu WB. Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols. Molecules. 2020 Feb 14;25(4) PubMed PMID: 32075144.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols. AU - Wu,Lin-Yang, AU - Usman,Muhammad, AU - Liu,Wen-Bo, Y1 - 2020/02/14/ PY - 2020/01/15/received PY - 2020/02/01/revised PY - 2020/02/12/accepted PY - 2020/2/21/entrez PY - 2020/2/23/pubmed PY - 2020/11/20/medline KW - BINOL synthesis KW - asymmetric catalysis KW - iron catalysis KW - nitrogen ligand KW - oxidative coupling JF - Molecules (Basel, Switzerland) JO - Molecules VL - 25 IS - 4 N2 - An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1'-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)-N1,N2-di(quinolin-8-yl)cyclohexane-1,2-diamine, L1]. A number of ligands (L2-L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/32075144/Enantioselective_Iron/Bisquinolyldiamine_Ligand_Catalyzed_Oxidative_Coupling_Reaction_of_2_Naphthols_ DB - PRIME DP - Unbound Medicine ER -