Borane Catalyst Hydrosilylation of Furan Derivatives

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Solution Overview

Problem

Current methods for producing silane derivatives from furan derivatives using metallic catalysts face challenges in achieving high yield and stereoselectivity under eco-friendly and mild conditions, making them unsuitable for commercial mass production.

Innovation Solution

A method involving the use of a borane catalyst for hydrosilylation of furan derivatives to produce silane derivatives with high stereoselectivity and yield, allowing for the synthesis of anti-(2-alkyl)cyclopropyl silane derivatives as important intermediates for medicines and agricultural chemicals.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If metallic catalysts are used for hydrosilylation of furan derivatives, then the reaction can proceed, but the yield and stereoselectivity are insufficient and the conditions are not eco-friendly

Engineering Contradiction:
Improveyield and stereoselectivityVSAvoidenvironmental friendliness
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces borane compounds as intermediary catalysts to mediate the hydrosilylation reaction between furan derivatives and silane compounds. The borane catalyst acts as a mediator that enables the reaction to proceed with high yield and stereoselectivity under mild and eco-friendly conditions, replacing the traditional metallic catalysts that caused environmental harm and poor reaction outcomes.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If traditional metallic catalysts are used, then the reaction can occur, but high yield and stereoselectivity under mild conditions cannot be achieved

Engineering Contradiction:
ImprovestereoselectivityVSAvoidreaction condition mildness
Core Design Contradiction:
Manufacturing precisionVSTemperature

Solution Approach 1:

The patent changes the catalytic parameter from metallic catalysts to borane compounds, which fundamentally alters the reaction parameters. This parameter change enables the reaction to proceed with high stereoselectivity under mild temperature conditions (room temperature or slightly elevated), avoiding the harsh conditions required by traditional metallic catalysts.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If metallic catalysts are used for commercial mass production, then production can occur, but the process is not economical due to low yield

Engineering Contradiction:
Improvecommercial mass production capabilityVSAvoidyield
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent employs borane compounds as disposable catalysts that can be used in small amounts (0.01-5 mol%) to achieve high yields. The borane catalyst, while potentially single-use or limited in stability, is employed in such small quantities that it becomes economically viable for mass production, contrasting with metallic catalysts that require higher amounts and achieve lower yields.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

4Quantity of substance

If conventional methods are used, then the reaction can proceed, but high conversion yield and stereoselectivity cannot be simultaneously achieved

Engineering Contradiction:
Improveconversion yieldVSAvoidstereoselectivity
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent creates a composite catalytic system by combining borane compounds with specific additives or using modified borane structures (such as borane-thf complexes or borane-hydrocarbon adducts). This composite approach enhances both the conversion yield and stereoselectivity simultaneously, achieving what neither component could accomplish alone.

Inventive Principle:
Principle #40Composite materials

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 method enables the commercial mass production of silane derivatives with high yield and stereoselectivity under mild conditions, utilizing borane catalysts to overcome the limitations of traditional methods, making the process more economical and environmentally friendly.

Implementation Method 1

a method of preparing a silane derivative from various furan derivatives in the presence of a borane catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10662206B2Method for preparing silane derivatives from furan derivatives in presence of borane catalyst
Publication Date: 2020.05.26 INST FOR BASIC SCI
  • US10662206B2 patent drawing
  • US10662206B2 patent drawing
  • US10662206B2 patent drawing

AI summary

The present invention relates to a method for preparing various silane derivatives by subjecting various furan derivatives to hydrosilylation in the presence of a borane catalyst. The method for preparing silane derivatives according to the present invention is a very efficient method for converting, into high value-added silane derivatives, various furan derivatives derived from biomass.