Fluorine-Substituted Boronic Acid Esters for Solubility

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Solution Overview

Problem

Aromatic diboronic acid ester compounds face challenges with poor solubility in organic solvents and high melting points, making them difficult to purify and use effectively in polymer materials.

Innovation Solution

A fluorine-containing boronic acid ester compound is synthesized through the reaction of a fluorine-containing 3,5-dihalogenoanilide derivative with a dialkoxyborane using a Group-10 transition metal catalyst, resulting in a compound with improved solubility and a low-melting-point solid or liquid form.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If aromatic diboronic acid ester compounds are used, then they are stable in water and air and suitable for cross-coupling reactions, but they have poor solubility in organic solvents and very high melting points

Engineering Contradiction:

Improvestability in water and airVSAvoidsolubility in organic solvents

Core Design Contradiction:

ReliabilityVSEase of operation

Solution Approach 1:

The patent introduces fluorine atoms at specific positions (3 and 5) of the aromatic ring to locally modify the molecular properties. This localized fluorine substitution improves solubility in organic solvents and reduces melting points while maintaining the overall stability and cross-coupling reactivity of the boronic acid ester compound

Inventive Principle:

Principle #3Local quality

Solution Approach 2:

The patent changes the molecular parameters by introducing fluorine-containing groups and adjusting the alkoxide substituents on the boron atom. These parameter changes result in compounds with melting points of 0 to 150°C and improved solubility, while preserving the essential chemical stability and reactivity needed for Suzuki-Miyaura reactions

Inventive Principle:

Principle #35Parameter changes

2Speed

If aromatic diboronic acid ester compounds are heated, then the reaction rate increases, but they are converted into boroxine and reactivity is reduced

Engineering Contradiction:

Improvereaction rateVSAvoidreactivity

Core Design Contradiction:

SpeedVSReliability

Solution Approach 1:

The patent applies preliminary anti-action by introducing fluorine atoms that sterically and electronically protect the boronic acid ester group from premature cyclization to boroxine. This prevents the harmful side reaction before it can occur, allowing the compound to maintain its reactivity even under heating conditions required for cross-coupling reactions

Inventive Principle:

Principle #9Preliminary anti-action

3Adaptability or versatility

If aromatic diboronic acid ester compounds are synthesized, then they can be used as starting materials for polymer production, but they are difficult to purify due to boroxine impurity formation

Engineering Contradiction:

Improveuse as starting material for polymer productionVSAvoidpurification difficulty

Core Design Contradiction:

Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent converts the potential harm of boroxine formation into a benefit by designing fluorine-containing compounds where the fluorine atoms prevent boroxine formation in the first place. This eliminates the purification problem while maintaining the compound's utility as a starting material for conjugated polymer production

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 fluorine-containing boronic acid ester compound exhibits high solubility in organic solvents and a low melting point, enabling its use as a starting material for conjugated polymer production and as a curing agent for elastomeric materials with enhanced chemical, heat, and low-temperature resistance.

Implementation Method 1

The fluorine-containing boronic acid ester compound is produced by the reaction of a fluorine-containing 3,5-dihalogenoanilide derivative represented by the general formula (2) with a dialkoxyborane represented by the general formula (3)

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2325188B1Fluorine-containing boronic acid ester compound and method for producing same

Publication Date: 2013.06.05 UNIMATEC CO LTD

AI summary

A fluorine-containing boronic acid ester represented by the general formula : (R1 is a linear or branched divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms, R2 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or phenyl group, n is an integer of 1 to 3, and m is an integer of 0 to 4) having an improved solubility in organic solvents is produced by reacting a fluorine-containing 3,5-dihalogenoanilide derivative represented by the general formula: (R2 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or phenyl group , X is a halogen atom, n is an integer of 1 to 3, and m is an integer of 0 to 4) with a dialkoxyborane represented by the general formula: (R1 is a linear or branched divalent aliphatic hydrocarbon group having 2 to 10 carbon atoms).