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Updated: Aug 15, 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
Polydentate hydrazones as multitasking catalysts in visible-light-induced coupling reactions of amines
Ganghu Wang1, Jianhua Zhang2, Legen Hu1
1School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, PR China. zhucycn@gmail.com.
Abstract:
A Cu/hydrazone catalyst has been applied in the coupling reactions of anilines for the synthesis of diarylamines and azobenzenes. The copper complex that is formed in situ plays a double duty by harnessing photon energy as a photocatalyst and then by catalysing organometallic elementary steps as a transition metal catalyst. By the selection of hydrazones and bases, the reaction selectivity of aniline can be tuned between homo-coupling and its cross-coupling with arylboronic acid, exhibiting the great potential of such hydrazones in organic synthesis.
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Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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...