Related Experiment Video
Updated: Sep 2, 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
Pyrimidopteridine-catalyzed Photo-mediated Hydroacetoxylation
Andranik Petrosyan1, Luisa Zach1, Tobias Taeufer1
1Leibniz Institute for Catalysis, Albert-Einstein-Str. 29a, 18059, Rostock, Germany.
This study introduces a novel photoredox catalyst for adding carboxylic acids to alkenes. The pyrimidopteridine catalyst enables hydroacetoxylation, overcoming typical decarboxylation challenges in this reaction.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Synthetic Methodology
Background:
- Carboxylic acids often undergo decarboxylation upon single-electron oxidation.
- Developing efficient methods for functionalizing alkenes remains a key challenge in organic synthesis.
Purpose of the Study:
- To report a novel photo-mediated formal addition of carboxylic acids to activated alkenes.
- To investigate the catalytic activity of a pyrimidopteridine photoredox catalyst in this transformation.
Main Methods:
- Utilized a pyrimidopteridine photoredox catalyst.
- Employed activated alkenes and aliphatic carboxylic acids.
- Conducted cyclic voltammetry (CV) measurements.
- Performed competitive Stern-Volmer quenching experiments.
- Carried out electron paramagnetic resonance (EPR) spectroscopy.
Main Results:
- Achieved a hydroacetoxylation of activated alkenes in the presence of carboxylic acids.
- Demonstrated that the pyrimidopteridine catalyst effectively counters decarboxylation.
- Provided mechanistic insights through electrochemical and spectroscopic studies.
- Showcased tetra-N-substituted pyrimidopteridines acting as dual photoredox and hydrogen atom transfer catalysts.
Conclusions:
- Established a new synthetic route for the formal addition of carboxylic acids to alkenes.
- Highlighted the efficacy of pyrimidopteridine photoredox catalysts in promoting challenging transformations.
- Confirmed the dual catalytic role of tetra-N-substituted pyrimidopteridines in the observed reaction.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
![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)
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
01:26Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
02:47Alkynes 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.
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...