Related Experiment Video
Updated: Oct 25, 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
Photoredox α-Alkylation of Phosphonates by Styrenes
Egor A Drokin1, Vladimir A Abramov1, Maxim A Topchiy1,2
1A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninskiy prospect 29, Moscow119991, Russia.
Abstract:
A new protocol for photocatalyzed regioselective α-alkylation of alkyl phosphonates with styrenes without the use of transition metals has been developed. The monoalkylation reaction occurs in 10 min using 0.1 mol % of the 4DPAFIPN photocatalyst. Conditions for the double addition of styrenes to phosphonates have also been found, enabling the regioselective addition of two different styrenes to a phosphonate. This method provides high yields and good tolerance of functional groups. This protocol has also been successfully applied on a gram scale.
Related Concept Videos
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
α-Alkylation of Ketones via Enolate Ions
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
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.
