Dinuclear Copper Catalyst C-H Oxidation via Redox Cycling

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Solution Overview

Problem

There is a need for synthetic catalysts that can mimic the functionality of copper-containing proteins to catalyze crucial biological and industrial conversions, particularly for C—H activation reactions and oxidation/oxygenation processes, which are relevant to both pharmaceutical and industrial applications.

Innovation Solution

The development of dinuclear copper complexes that cycle between a resting Cu(I) state and a catalytically active Cu(II) state, utilizing bidentate or multidentate ligands and a stabilizing counter ion, enabling oxidation or oxygenation of substrates containing C—H bonds through a μ-OH group that forms hydrogen bonds with the counter ion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If natural copper-containing proteins are used for C-H activation and oxidation reactions, then high catalytic activity and selectivity are achieved, but complexity in isolation, characterization, and application is increased

Engineering Contradiction:

Improvecatalytic activityVSAvoidcomplexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent creates simplified synthetic copper complexes that copy the essential catalytic features of natural metalloproteins. The dinuclear copper complexes with bidentate or multidentate ligands replicate the active site geometry and electronic structure needed for C-H activation, achieving comparable catalytic activity without the complexity of full protein structures

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The patent extracts only the essential catalytic components from natural metalloproteins - specifically the copper centers and their coordination environment - while removing the complex protein backbone. This allows the core catalytic function to be preserved in a simplified molecular complex that is easier to characterize and apply

Inventive Principle:

Principle #2Taking out (Extraction)

2Ease of manufacture

If synthetic copper complexes are designed to mimic metalloprotein functionality, then ease of manufacture and application is improved, but catalytic activity and selectivity may be reduced

Engineering Contradiction:

Improveease of preparationVSAvoidcatalytic activity

Core Design Contradiction:

Ease of manufactureVSReliability

Solution Approach 1:

The patent systematically varies ligand parameters (bite angle, donor strength, steric bulk) and copper oxidation states to optimize catalytic activity. By changing these molecular parameters, the synthetic complexes achieve both ease of preparation through simple synthesis routes and high catalytic performance through rational molecular design

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite-like structures where copper centers are combined with specially designed organic ligands (bidentate or multidentate) to form dinuclear complexes. This composite approach allows the benefits of both metal catalysis and organic structure tuning, achieving high activity while maintaining ease of manufacture

Inventive Principle:

Principle #40Composite materials

3Adaptability or versatility

If dinuclear copper complexes with bidentate or multidentate ligands are used for oxidation reactions, then catalytic versatility is improved, but device complexity is increased

Engineering Contradiction:

Improvecatalytic versatilityVSAvoidstructural complexity

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent designs dinuclear copper complexes with bidentate or multidentate ligands that can perform multiple catalytic functions - C-H activation, oxidation, and oxygenation reactions. The same core structure serves as a universal platform for different transformations by adjusting reaction conditions and substrates, achieving versatility without proportional increases in complexity

Inventive Principle:

Principle #6Universality (Multi-functionality)

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 provides a cost-effective and sustainable method for catalyzing oxidation or oxygenation reactions, allowing for the conversion of low-grade hydrocarbons into valuable chemicals, with the catalyst being easy to prepare and tune for specific applications.

Implementation Method 1

the bi-copper center comprises a μ-OH that can form a hydrogen bond with the stabilizing counter ion

Methodology Applied

Scientific EffectHydrogen bond:

Implementation Method 2

one or more copper atoms that can convert between a resting state (a reduced oxidation state) and a catalytically-active state (oxidized state)

Methodology Applied

Scientific EffectRedox reactions: Redox Reactions

Data Source

PatentUS11795129B2Dinuclear copper catalyst for the oxidation/oxygenation of hydrocarbons

Publication Date: 2023.10.24 FLORIDA INTERNATIONAL UNIVERSITY

AI summary

The subject invention provides synthetic compounds, and compound complexes having catalytic activities towards oxidation or oxygenation, and/or dehydrogenation of various substrates comprising C−H bonds. The catalysts of the subject invention comprise a dinuclear Cu(I)/Cu(II) center that can convert between a resting state and a reactive species. The subject invention also provides methods of using such catalysts for the oxidation of substrates comprising C−H bonds, e.g., hydrocarbons, to synthesize chemicals for use as pharmaceuticals and industrial feedstock.