Group 10 Catalyst Ligand Design for Trifluoropropene Synthesis
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Solution Overview
Problem
Current processes for producing 2-(substituted phenyl)-3,3,3-trifluoropropene compounds face challenges in achieving high yield and industrial scalability, with existing methods often resulting in low yields and impractical use of arsenic compounds as ligands.
Innovation Solution
A process involving the reaction of substituted phenylboronic acid or its ester/salt with a 2-halogen-3,3,3-trifluoropropene compound using a complex catalyst system, specifically a Group 10 metal catalyst with phosphine or carbene ligands, to enhance yield and selectivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional Suzuki-Miyaura coupling reaction is used with substituted phenylboronic acid and Group 10 transition metal catalyst, then the reaction can proceed to produce 2-(substituted phenyl)-3,3,3-trifluoropropene compound, but the yield is limited to 49-73% and the process is not suitable for industrial production
Solution Approach 1:
The patent changes the catalyst parameters by introducing specific phosphine ligands (formula 2) with modified structural parameters (R1-R6 groups) to the Group 10 transition metal center, thereby optimizing the catalytic activity and selectivity to achieve high yields suitable for industrial production
Solution Approach 2:
The patent creates a composite catalyst system combining Group 10 transition metal with specifically designed phosphine ligands (formula 2), where the ligand structure comprises a central core with substitutable groups R1-R6, forming a composite material that enhances both yield and industrial scalability
2Productivity
If arsenic compound is used as ligand in the coupling reaction, then the reaction can proceed, but the process becomes impracticable for industrial application
Solution Approach 1:
The patent replaces toxic arsenic ligands with phosphine ligands (formula 2) that are less toxic and more suitable for industrial application, while maintaining or improving the reaction efficiency through optimized ligand structure
Solution Approach 2:
The patent introduces phosphine ligands as intermediary compounds that mediate the coupling reaction between substituted phenylboronic acid and 2-halogen-3,3,3-trifluoropropene compound, replacing the harmful arsenic compound intermediary
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 process enables the production of 2-(substituted phenyl)-3,3,3-trifluoropropene in high efficiency and selectivity, reducing catalyst usage and facilitating industrial production as an intermediate for medicines and pesticides.
Implementation Method 1
by reacting a substituted phenylboronic acid or a substituted phenylboronic ester or a substituted phenylboronic acid salt represented by the formula (1) with a 2-halogen-3,3,3-trifluoropropene compound or salt thereof, the compound being represented by the formula (2), in the presence of a complex catalyst represented by the formula (3)
Data Source
AI summary
There is provided a novel process for production of a 2-(substituted phenyl) -3,3,3-trifluoropropene.Disclosed is a process for production of a 2-(substituted phenyl)-3,3,3-trifluoropropene compound represented by the formula (7) or a salt thereof The process comprises reacting a compound represented by the formula (1) (X is an alkyl group, etc.) with a compound represented by the formula (2) (Y is a halogen atom, etc.) in the presence of a catalyst represented by the formula (3) (M is an ion of a metal belonging to Group 10 on the elementary periodic table which has an oxidation state number of 1 to 8; G is a unidentate or multidentate ligand; L is a phosphine compound represented by the formula (4) which is bound to the center metal M or is a carbene selected from those represented by the formulae (5) and (6), provided that L's may be same as or different from one another when a is 2 to 5; A represents a univalently or multivalently charged anion; b represents an integer of 1 to 3; a represents an integer of 1 to 5·b; c represents 0 or an integer of 1 to 4·b; and n represents an integer of 1 to 6).