Immobilized Pd Catalyst for Cross-Coupling Separation
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Solution Overview
Problem
Current cross-coupling reactions using immobilized organometallic complexes on carriers face challenges in achieving high yields with a small amount of catalyst and short reaction time, particularly in C—N cross-coupling reactions, where the separation of catalyst from the product is difficult and the use of halogen-substituted benzene derivatives can reduce raw material costs but requires improvement in yield and efficiency.
Innovation Solution
A catalyst system comprising a synthetic resin carrier with an organometallic complex immobilized by chemical bonding, where the complex has a Pd coordination center and a structure featuring a silyl group bonded to the backbone carbon of an NHC imidazole ring, allowing for efficient immobilization and high catalytic activity, thereby improving yield and reaction time.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If an organometallic complex catalyst is used in cross-coupling reactions, then high catalytic activity is achieved, but separation of the catalyst from the product becomes difficult
Solution Approach 1:
The catalyst system is segmented into two distinct parts: a soluble organometallic complex that provides catalytic activity and an immobilized ligand component that remains on the carrier. This segmentation allows the catalytically active species to function in solution while the supporting structure remains fixed, enabling easy separation of the catalyst from the product through filtration or decantation.
Solution Approach 2:
A carrier material serves as an intermediary between the soluble organometallic complex and the reaction medium. The carrier immobilizes certain components of the catalyst system while allowing the active catalytic species to remain in solution, thus mediating between the need for high catalytic activity and ease of separation.
2Quantity of substance
If halogen-substituted benzene derivatives are used as substrates, then raw material costs are reduced, but reaction efficiency and yield require improvement
Solution Approach 1:
The invention optimizes reaction parameters including temperature, solvent selection, base type, and catalyst composition to enhance the reactivity of halogen-substituted benzene derivatives. By adjusting these parameters, the system achieves high reaction efficiency and yield even with less reactive substrates like chlorobenzenes, thereby reducing raw material costs without sacrificing productivity.
3Quantity of substance
If a small amount of catalyst is used, then cost efficiency improves, but achieving high yield in short reaction time becomes challenging
Solution Approach 1:
The catalyst system is designed to maintain continuous catalytic activity throughout the reaction process. The immobilized ligand on the carrier provides sustained support for the organometallic complex, ensuring that even at low catalyst loadings, the reaction proceeds efficiently and continuously to achieve high yields in short reaction times.
Solution Approach 2:
The catalyst system employs a composite structure combining an organometallic complex with an immobilized ligand on a carrier material. This composite approach enhances the catalytic activity per unit of catalyst, allowing high productivity to be achieved with minimal catalyst quantities.
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 catalyst enables high-yield production of cross-coupling products in a short reaction time with a small amount of catalyst, effectively addressing the separation issues and cost reduction in raw materials by ensuring the organometallic complex remains immobilized and maintains catalytic activity.
Implementation Method 1
an organometallic complex immobilized by chemical bonding on a synthetic resin (precursor)
Data Source
AI summary
It is an object of the present invention to provide a catalyst for a cross-coupling reaction in which an organometallic complex is sufficiently immobilized on a carrier and an object product can be easily obtained in a high yield and in a relatively short reaction time with a relatively small amount of use. The catalyst for a cross-coupling reaction of the present invention has a carrier part composed of a synthetic resin and an organometallic complex part immobilized on the carrier part by chemical bonding, and has a structure represented by formula (P1), wherein in (P1) R1, R2 may be the same or different, and is a substituent such as a hydrogen atom. R3, R4, R5, R6, R8, R9 may be the same or different and are substituents, such as a hydrogen. X represents a halogen atom, and R7 represents a substituent having 3 to 20 carbon atoms with a π bond. RS1 represents the main chain of the synthetic resin precursors having —CH2OH group at their end.