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Updated: May 14, 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
Photoinduced Copper-Catalyzed Regio- and Diastereoselective Multicomponent [3 + 2 + 1] Radical Cyclization To Access
Sijia Li1, Jianye Li1, He Zhang1
1CCNU-uOttawa Joint Research Centre, State Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Abstract:
The use of simple raw materials to construct complex piperidine scaffolds via multicomponent reactions is highly desirable from the perspectives of atom and step-economy. In this Letter, we present a photoinduced copper-catalyzed three- or four-component [3 + 2 + 1] radical cyclization, utilizing inexpensive and readily available feedstock amines, alkynes, and aldehydes, to synthesize multisubstituted bicyclic or spirocyclic tetrahydropyridines. This method is notable for its mild conditions, atom-economic approach, excellent regio- and diastereoselectivity, and the simultaneous activation of two α-amino C(sp3)-H bonds, resulting in the formation of three C-C bonds and one C-N bond in a single step. Mechanistic studies suggest that the α-aminoalkyl radical is the key intermediate in this reaction, which undergoes sequential radical addition, 1,5-HAT, and 6-exo-trig-type radical cyclization.
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