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Open AccessArticle

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

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
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Author to whom correspondence should be addressed.
Academic Editors: Hans-Joachim Knölker and Jean-Luc Renaud
Molecules 2020, 25(4), 852; https://doi.org/10.3390/molecules25040852 (registering DOI)
Received: 15 January 2020 / Revised: 1 February 2020 / Accepted: 12 February 2020 / Published: 14 February 2020
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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 (L2L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.
Keywords: iron catalysis; asymmetric catalysis; nitrogen ligand; oxidative coupling; BINOL synthesis iron catalysis; asymmetric catalysis; nitrogen ligand; oxidative coupling; BINOL synthesis
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MDPI and ACS Style

Wu, L.-Y.; Usman, M.; Liu, W.-B. Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols. Molecules 2020, 25, 852.

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