Related Experiment Video
Updated: Jun 9, 2026
![[(DPEPhos)(bcp)Cu]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)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Copper Photoredox Catalyzed A3' Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom
Arunachalam Sagadevan1, V Kishore Kumar Pampana1, Kuo Chu Hwang1
1Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, R.O.C.
Abstract:
The first successful example of the three-component coupling of N-alkylanilines, terminal alkynes, and alcohols was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox hydrogen-atom transfer process. This method allows preparation of propargylamines through uniquely selective α-C-H bond activation of unactivated alkylalcohols. Preliminary studies indicate that formation of α-oxy radical is operative. This approach facilitates rapid access to biologically important propargylamines from methanol as an abundant feedstock.
Related Concept Videos
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...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

![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)