Related Experiment Video
Updated: Jun 3, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photoredox/Sulfide Dual Catalysis for Modular Synthesis of Multi-substituted Furan Rings via Catalytic Indirect
Kakeru Matsukuma1, Masanori Tayu1, Takumi Ogino1
1Department Laboratory of Organic and Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan.
Abstract:
The catalytic indirect reductive quenching method is facilitated by a combination of Ir(III) photoredox and sulfide dual-catalysis system. This study demonstrated a method for synthesizing multi-substituted furans by using a photoredox/sulfide dual-catalysis system. This method enables the synthesis of various furan derivatives, including spirofurans and phthalans. The utility of this system was demonstrated through gram-scale synthesis of the pharmaceutical molecule talopram. Mechanistic studies and density functional theory calculations suggested the formation of sulfonium species via sulfide radical cations, followed by intramolecular cyclization to produce the desired furan derivatives.
Related Concept Videos
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
