Copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes
- 5 January 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 19 (5), 988-992
- https://doi.org/10.1039/d0ob02514c
Abstract
A copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes in the presence of di-tert-butyl peroxide (DTBP) was developed via a radical reaction process. Various alkanes and aromatic or aliphatic amines with diverse structures and electronic properties are suitable substrates, and the chirality of amines can be maintained for the transformation. This method has high step and atom economy for straightforward access to aminated and alkylated quinones from readily available starting materials.Keywords
Funding Information
- Chinese Academy of Sciences
- Applied Basic Research Program of Sichuan Province (20YYJC0492)
This publication has 68 references indexed in Scilit:
- Hydroquinone-Benzoquinone Redox Couple as a Versatile Element for Molecular ElectronicsThe Journal of Physical Chemistry C, 2013
- 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
- Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agentsEuropean Journal of Medicinal Chemistry, 2010
- Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapacholBioorganic & Medicinal Chemistry, 2010
- Palladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsChemical Reviews, 2010
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie, 2009
- A Vaulted Biaryl Phosphoric Acid-Catalyzed Reduction of α-Imino Esters: The Highly Enantioselective Preparation of α-Amino EstersJournal of the American Chemical Society, 2007
- Cruciform π-Systems for Molecular Electronics ApplicationsJournal of the American Chemical Society, 2003
- Regioselective Double Alkylation of Styrenes with Alkyl Halides Using a Titanocene CatalystJournal of the American Chemical Society, 1998
- Synthesis of miltirone by an ultrasound-promoted cycloadditionThe Journal of Organic Chemistry, 1990