Heterocyclic Carboxylic Acid Amide Ligand for Copper Catalyzed Aryl Chloride Coupling
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Solution Overview
Problem
Current copper-catalyzed coupling reactions for aryl chlorides are inefficient due to the high energy of the C-Cl bond, requiring expensive palladium catalysts and complex ligands, and lack a simple, cost-effective catalytic system suitable for industrial applications.
Innovation Solution
A catalytic system using a specific heterocyclic carboxylic acid amide ligand with a copper catalyst, base, and organic solvent, optimized for copper-catalyzed coupling reactions of aryl chlorides to form C-N, C-O, and C-S bonds, which simplifies the reaction conditions and reduces the need for expensive ligands and catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If copper catalyst is used for coupling reaction of aryl chlorides, then cost is reduced and availability is improved, but reaction efficiency is insufficient and substrate scope is limited
Solution Approach 1:
The patent changes the chemical parameters of the catalytic system by introducing heterocyclic carboxylic acid amide ligands with specific structural features (electron-donating groups, heteroatom composition) to modify the copper catalyst's activity and expand substrate scope while maintaining cost-effectiveness
Solution Approach 2:
The patent creates a composite catalytic system combining copper catalyst with heterocyclic carboxylic acid amide ligands, where the ligand-copper complex exhibits enhanced catalytic activity for aryl chloride coupling reactions compared to copper alone
2Productivity
If palladium catalyst with complex phosphine ligands is used, then coupling reaction efficiency is improved, but cost increases and device complexity increases
Solution Approach 1:
The patent replaces expensive palladium catalysts with cheaper copper catalysts that can be used in disposable quantities, eliminating the need for complex phosphine ligands while maintaining acceptable reaction efficiency through optimized copper-ligand complexes
Solution Approach 2:
The patent changes the catalyst type from palladium to copper and modifies ligand structure from complex phosphine to simpler heterocyclic carboxylic acid amide, achieving cost reduction and simplified system while maintaining catalytic functionality
3Ease of manufacture
If copper catalyst system is simplified, then cost is reduced and ease of manufacture is improved, but reaction efficiency decreases
Solution Approach 1:
The patent optimizes parameters of the simplified copper catalyst system by selecting specific heterocyclic carboxylic acid amide ligands with appropriate electron-donating groups and heteroatom composition to maintain reaction efficiency while keeping the system simple and cost-effective
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
The system enables efficient copper-catalyzed coupling reactions of aryl chlorides with various nucleophiles under mild conditions, offering good substrate compatibility and wide application prospects, while reducing costs and simplifying the preparation of ligands and catalysts.
Implementation Method 1
a copper-catalyzed coupling reaction of aryl halide catalyzed by a heterocyclic carboxylic acid amide ligand
Implementation Method 2
use of the following compound of formula (I) as a ligand for a copper-catalyzed coupling reaction
Data Source
AI summary
Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C-N, C-O, C-S and other bonds.