Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols

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 gener...

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Detalles Bibliográficos
Autores principales: Wu, Lin-Yang, Usman, Muhammad, Liu, Wen-Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070846/
https://www.ncbi.nlm.nih.gov/pubmed/32075144
http://dx.doi.org/10.3390/molecules25040852
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author Wu, Lin-Yang
Usman, Muhammad
Liu, Wen-Bo
author_facet Wu, Lin-Yang
Usman, Muhammad
Liu, Wen-Bo
author_sort Wu, Lin-Yang
collection PubMed
description 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(ClO(4))(2) and a bisquinolyldiamine ligand [(1R,2R)-N(1),N(2)-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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spelling pubmed-70708462020-03-19 Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols Wu, Lin-Yang Usman, Muhammad Liu, Wen-Bo Molecules Article 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(ClO(4))(2) and a bisquinolyldiamine ligand [(1R,2R)-N(1),N(2)-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. MDPI 2020-02-14 /pmc/articles/PMC7070846/ /pubmed/32075144 http://dx.doi.org/10.3390/molecules25040852 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wu, Lin-Yang
Usman, Muhammad
Liu, Wen-Bo
Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title_full Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title_fullStr Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title_full_unstemmed Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title_short Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
title_sort enantioselective iron/bisquinolyldiamine ligand-catalyzed oxidative coupling reaction of 2-naphthols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070846/
https://www.ncbi.nlm.nih.gov/pubmed/32075144
http://dx.doi.org/10.3390/molecules25040852
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AT usmanmuhammad enantioselectiveironbisquinolyldiamineligandcatalyzedoxidativecouplingreactionof2naphthols
AT liuwenbo enantioselectiveironbisquinolyldiamineligandcatalyzedoxidativecouplingreactionof2naphthols

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