Metal Catalyst for C-N Coupling Reducing Loading
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Solution Overview
Problem
Current C—N coupling methods require high catalyst loading, excessive use of bases or oxidants, and additional steps to adjust nitrogen reactivity, which are inefficient and costly, especially when using palladium-based catalysts.
Innovation Solution
A metal catalyst system represented by specific formulas involving Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru, with varying substituents, is used for C—H bond activation and C—N coupling under mild conditions without the need for oxidants or bases, allowing for efficient formation of C—N bonds between sp3 carbon and primary or secondary amines.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If palladium-based catalysts are used for C-N coupling, then good reaction yields are achieved, but high catalyst loading and excessive use of bases or oxidants are required
Solution Approach 1:
The patent changes the chemical parameters of the catalyst system by introducing specific ligand structures (compounds of formula I or II) that modify the electronic and steric properties of the metal center. This allows the catalyst to achieve high activity at lower loadings (0.1-10 mol%) compared to conventional palladium catalysts, directly resolving the contradiction between yield and catalyst quantity
Solution Approach 2:
The patent creates composite catalyst systems by combining metal centers (Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru) with specifically designed organic ligands (formula I or II). These composite structures exhibit synergistic effects where the ligand modifies the metal's reactivity, enabling efficient C-N coupling at low catalyst loading without requiring excessive bases or oxidants
2Reliability
If nitrogen reactivity is adjusted by forming bonds with halogens or carboxylic acids, then electrophilic nitrogen is achieved, but additional synthetic steps are required
Solution Approach 1:
The patent enables the nitrogen atom to perform its nucleophilic function directly without requiring pre-synthetic modification. The catalyst system itself creates the necessary reactive intermediates, allowing the amine to couple with the hydrocarbon in a single step, thus eliminating the need for additional synthetic steps while maintaining reliable C-N bond formation
Solution Approach 2:
The metal catalyst acts as an intermediary that facilitates the interaction between the nucleophilic nitrogen and the hydrocarbon substrate. The catalyst generates electrophilic metal-carbon intermediates that can be attacked by the nitrogen, providing an alternative pathway that avoids direct modification of the nitrogen atom while achieving the same coupling outcome
3Manufacturing precision
If conventional C-H activation methods are used, then C-N bond formation is facilitated, but nucleophilic nitrogen and leaving group requirements increase process complexity
Solution Approach 1:
The patent develops a universal catalyst system that can activate C-H bonds and facilitate C-N coupling without requiring specific leaving groups or additional functional groups on the substrates. The catalyst (formula I or II) performs multiple functions: C-H activation, intermediate stabilization, and C-N bond formation, simplifying the overall process while maintaining high manufacturing precision
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This approach significantly reduces catalyst loading, eliminates the need for additional reagents, and achieves high yields of aliphatic and aromatic amines, including cyclic compounds, under ambient conditions, thereby enhancing atom economy and reducing production costs.
Implementation Method 1
a metal catalyst for C—H bond activation and/or C—N coupling reaction
Implementation Method 2
C—H bond activation and/or C—N coupling reaction
Data Source
AI summary
A method for C—H bond activation and/or C—N coupling reaction comprises adding a hydrocarbon material to a container; adding a metal catalyst to the container; adding a primary or a secondary amine to the container. The metal catalyst is represented by the following formula:where Q is a 5 or 6 membered aromatic ring; W, X, and Y are the same or different, and are independently N, S, P, or O; M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; Z is halide (F, Cl, Br, or I); R1 and R2 are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl; and n is 1, 2, or 3.