Related Experiment Video
Updated: Oct 15, 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
The acridone anion as a highly reducing visible-light photocatalyst
Alejandro Heredero Sánchez1, Burkhard König1, Indrajit Ghosh1,2
1Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany. burkhard.koenig@ur.de.
Abstract:
Highly reducing photocatalysts enable the activation of strong chemical bonds under mild conditions. Here, we report that, upon visible-light excitation, deprotonated acridone generates a highly reducing excited state that activates (hetero)aryl halides, including chlorides, for C-B, C-P, C-S, and C-C bond formation, and, in combination with nickel catalysis, enables C-N bond formation. Mechanistic studies confirm that the excited-state acridone anion is capable of a single-electron transfer to aryl halides for bond activation.
Related Concept Videos
Nitriles to Amines: LiAlH4 Reduction
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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.
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
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...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
![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)
