Related Experiment Video
Updated: May 24, 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
In situ selective N-alkylation of pendant pyridyl functionality in mixed-valence copper complexes with methanol and
Da-Qian Feng1, Xiao-Ping Zhou, Ji Zheng
1Department of Chemistry, Shantou University, Guangdong 515063, P. R. China.
Abstract:
The reactions of CuBr(2) with pyridyl 2,2':6',2''-terpyridine ligands in methanol yielded four copper complexes under solvothermal conditions. The self-assembly processes were accompanied by designing bitopic precursor ligands and increasing the stoichiometric metal-ligand ratio. In the four resulting complexes, the pendant pyridyl groups of pyridylterpyridine were selectively in situ N-methylated and yielded the 4'-(N-methylpyridinium)-2,2':6',2''-terpyridine cations, including the 2-position pyridyl group which is difficult to be N-alkylated due to the steric problem. Partial divalent copper atoms were reduced to cuprous ones in the solvothermal reactions, which made the mixed-valence copper atoms coexist in each compound. The mixed-valence complexes have a varied dimensionality (from 2D to 0D) and the Cu(I)Br cluster, which can be controlled by changing the metal-ligand ratio. Theoretical studies show that the nucleophilic attack of the nitrogen atom in the pendant pyridyl is more facile than others of terpyridine. A possible mechanism was also proposed.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
09:35Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
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.
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Radical Substitution: Allylic Bromination
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.
Preparation and Reactions of Sulfides
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...