Silver-Catalyzed Three-Component Difunctionalization of Alkenes via Radical Pathways: Access to CF3-Functionalized Alkyl-Substituted 1,4-Naphthoquinone Derivatives
- 28 December 2018
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 84 (2), 1006-1014
- https://doi.org/10.1021/acs.joc.8b02997
Abstract
A silver-catalyzed three-component difunctionalization of alkenes by using 2-amino- and 2-hydroxyl-1,4-naphthoquinone derivatives as the radical-trapping reagents is reported. Various alkenes and 2-amino- or 2-hydroxyl-1,4-naphthoquinones with diverse structures and electronic properties are applied to the reaction. The methodology provides an alternative method to access CF3-functionalized alkyl-substituted quinone derivatives which are prevalent structures in bioactive molecules. Besides, a plausible radical pathway for the reaction is proposed based on results from primary control experiments.Keywords
Funding Information
- Ministry of Science and Technology of the People's Republic of China (2017YFD0200504)
- China Agricultural University
- College of Science, China Agricultural University
This publication has 69 references indexed in Scilit:
- Copper‐Catalyzed Intermolecular Aminocyanation and Diamination of AlkenesAngewandte Chemie, 2013
- Cytotoxic and antioxidant marine prenylated quinones and hydroquinonesNatural Product Reports, 2012
- A Novel Class of Small Molecule Inhibitors of HDAC6ACS Chemical Biology, 2011
- C−H Functionalization of 1,4-Naphthoquinone by Oxidative Coupling with Anilines in the Presence of a Catalytic Quantity of Copper(II) AcetateThe Journal of Organic Chemistry, 2011
- Organocatalyzed Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-KetophosphonatesθThe Journal of Organic Chemistry, 2011
- Chiral (thio)phosphorodiamides as excellent hydrogen bond donor catalysts in the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefinsChemical Communications, 2011
- Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffoldBioorganic & Medicinal Chemistry, 2009
- Total Syntheses of Cytotoxic, Naturally Occurring Kalasinamide, Geovanine, and Marcanine AAngewandte Chemie, 2009
- Aerobic Oxidation of Hydroquinone Derivatives Catalyzed by Polymer‐Incarcerated Platinum CatalystAngewandte Chemie, 2008
- Organocatalytic Highly Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinones to NitroalkenesOrganic Letters, 2008