ArticleThe Journal of organic chemistry2018
Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Cooperative Copper/Lipase Catalysis for the Chemoenzymatic Dynamic Kinetic Resolution (DKR) of Bis(hetero)arenols.JACS Au · 2025Article
- Photocatalytic Oxidative Dimerization of Electronically Diverse Phenols Using Borate to Prevent Overoxidation.Journal of the American Chemical Society · 2025Article
- Total Syntheses of Clausenawallines A and E.Organic letters · 2024Article
- Recent advances in oxidative phenol coupling for the total synthesis of natural products.Natural product reports · 2024Review
- Article
- Applications of Vanadium, Niobium, and Tantalum Complexes in Organic and Inorganic Synthesis.ACS organic & inorganic Au · 2023Review
- Visible-Light-Induced Oxidative Coupling of Phenols and Alkenylphenols with a Recyclable, Solid Photocatalyst.Organic letters · 2023Article
- An Enantioselective Suzuki-Miyaura Coupling To Form Axially Chiral Biphenols.Journal of the American Chemical Society · 2022Article
- Catalytic Oxidative Coupling of Phenols and Related Compounds.ACS catalysis · 2022Article
- Article
- Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C-C and C-O Coupling.Angewandte Chemie (International ed. in English) · 2020Article
- Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products.Organic letters · 2020Article
- Diastereoselective Synthesis of Benzoxanthenones.Chemistry, an Asian journal · 2020Article
- Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.Angewandte Chemie (International ed. in English) · 2020Review
- Vanadium-Catalyzed Selective Oxidative Homocoupling of Alkenyl Phenols to Synthesize Lignan Analogs.ACS catalysis · 2019Article
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12 authors.
Funding
Abstract
The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Brønsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum mechanical studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.
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