Spirobenzylamine-phosphine Iridium Complex for Asymmetric Hydrogenation
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Solution Overview
Problem
Existing chiral ligands and catalysts for asymmetric hydrogenation of alpha-substituted acrylic acids require high hydrogen pressure, result in low enantioselectivity, and have limitations in substrate range and catalyst efficiency, making them unsuitable for practical industrial applications.
Innovation Solution
A new spirobenzylamine-phosphine iridium complex is synthesized through a two-step or three-step reaction, allowing for asymmetric hydrogenation of alpha-substituted acrylic acids at reduced pressure with high enantioselectivity and efficiency, using substituted 7-trifluoromesyloxy-7'-diarylphosphino-1,1'-spiro-dihydroindene as a raw material and complexing with an iridium precursor followed by ion exchange to achieve various anions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If existing chiral ligands and catalysts are used for asymmetric hydrogenation, then catalytic activity can be achieved, but high hydrogen pressure is required which creates safety problems and requires complex apparatus
Solution Approach 1:
The patent changes the chemical parameters of the catalyst system by introducing a new spirobenzylamine-phosphine ligand with specific molecular structure and electronic properties. This ligand modification alters the catalytic cycle parameters, enabling the reaction to proceed at lower hydrogen pressures (0.1-10 MPa) while maintaining high catalytic activity and enantioselectivity
Solution Approach 2:
The patent creates a composite catalyst system combining iridium metal center with spirobenzylamine-phosphine ligand and chiral auxiliary components. This composite structure synergistically enhances catalytic performance, allowing reduced hydrogen pressure operation while achieving both high activity and enantioselectivity that neither component could achieve alone
2Reliability
If existing catalysts are used, then hydrogenation can proceed, but enantioselectivity is reduced when hydrogen pressure is lowered
Solution Approach 1:
The patent modifies the chemical parameters of the ligand system to change the energy landscape of the catalytic cycle. The spirobenzylamine-phosphine ligand creates a more rigid chiral environment and optimizes substrate binding geometry, maintaining high enantioselectivity across a broader pressure range including lower pressures where conventional catalysts fail
3Adaptability or versatility
If existing chiral ligands are used, then asymmetric hydrogenation can be achieved, but the substrate range is limited and catalyst efficiency is reduced
Solution Approach 1:
The patent designs a universal catalyst system where the spirobenzylamine-phosphine ligand framework can accommodate various substrate types including alpha-aryl substituted acrylic acids and other alpha-substituted acrylic acids. The ligand's structural features provide broad substrate scope while maintaining high catalytic efficiency across different substrate classes
Solution Approach 2:
The patent optimizes catalyst parameters including ligand structure, metal center, and ancillary ligands to enhance both substrate scope and turnover frequency. The modified catalyst system achieves higher productivity with lower catalyst loading (0.001-1 mol%) while expanding applicability to diverse substrates
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 new iridium complex achieves high catalytic activity and enantioselectivity (up to 99% ee) at lower hydrogen pressures (0.6MPa), with broad substrate applicability and improved reaction efficiency, overcoming the limitations of previous catalysts.
Implementation Method 1
The new Iridium complex of spiro benzyl amine-phosphine may be used in in asymmetric hydrogenation of a variety of alpha-substituted acrylic acids
Implementation Method 2
asymmetric hydrogenation of a variety of alpha-substituted acrylic acids
Implementation Method 3
The spirobenzylamine-phosphine is complexed with an iridium precursor
Implementation Method 4
is subjected to ion exchange, to give an iridium complex comprising various anions
Data Source
AI summary
The present invention relates to a spirobenzylamine-phosphine, preparation method therefor and use thereof. The compound has a structure represented by formula (I), wherein n=0 to 3; R1, R2, R3, R4, R5, R6, R7, R8 and R9 having a value as defined in claim 1. Starting from the substituted 7-trifluoromesyloxy-7'-diarylphosphino-1, 1'-spiro-dihydroindene, the compound is synthesized in a two-step or three-step reactions. The new spirobenzylamine-phosphine is complexed with an iridium precursor and is subjected to ion exchange, to give an Iridium/spirobenzylamine-phosphine complex comprising various anions. The spiro benzyl amine-phosphine/Iridium complex according to the present invention may be used for catalyzing asymmetry hydrogenation of a variety of alpha-substituted acrylic acids, has high activity and enantio-selectivity, and has a good prospect of industrialization.