Triorganosilane Synthesis via Monotriflate for High-Yield Selectivity
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Solution Overview
Problem
Existing methods for producing triorganosilane compounds face issues such as low yield, formation of undesired isomers, and the need for high temperature conditions, particularly when introducing secondary aliphatic hydrocarbon or aryl groups, and inefficiencies with aryllithium reagents.
Innovation Solution
A method involving the reaction of a diorganosilane compound with a triflating reagent to form a monotriflate, followed by reaction with a metal reagent like R3Li or R3MgX to produce triorganosilane, and optionally converting aryl groups to cycloalkyl groups using a metal catalyst under controlled conditions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If a secondary aliphatic hydrocarbon group is introduced into di-t-butylsilane by the method in Non-Patent Document 2, then the triorganosilane compound can be produced, but the yield is medium and an undesired isomer is formed
Solution Approach 1:
The invention changes the reaction parameters by using a specific sequence of reactions: first forming a monolithium intermediate by reacting di-t-butylsilane with an organolithium reagent, then reacting this intermediate with an alkyl halide. This parameter change in the reaction pathway achieves both high yield and high isomer purity (95% or more) for the desired triorganosilane compound.
Solution Approach 2:
The invention segments the overall transformation into two distinct steps: (1) formation of the monolithium intermediate by reacting di-t-butylsilane with organolithium reagent, and (2) alkylation of the intermediate with alkyl halide. This segmentation allows each step to be optimized independently, achieving both high yield and high purity.
2Productivity
If an aryl group is introduced into di-t-butylsilane by the method in Non-Patent Document 3, then the triorganosilane compound can be produced, but a high temperature condition that is stirring under reflux by heating is required
Solution Approach 1:
The invention changes the reaction conditions by using a two-step process with the first step forming a monolithium intermediate at lower temperature, followed by alkylation at elevated temperature. This parameter change allows the reaction to proceed with good yield (80-90%) without requiring prolonged reflux heating, thus reducing energy consumption and improving productivity.
3Productivity
If aryllithium prepared from a halogenated aryl compound and n-butyllithium or sec-butyllithium reagent is used, then the aryl group introduction can be attempted, but the aryl group could not be efficiently introduced
Solution Approach 1:
The invention segments the aryl group introduction into two steps: (1) forming the monolithium intermediate by reacting di-t-butylsilane with aryllithium reagent, and (2) reacting this intermediate with an aryl halide. This segmentation significantly improves the efficiency and reliability of aryl group introduction compared to direct one-step methods.
Solution Approach 2:
The invention uses the monolithium intermediate as an intermediary species that facilitates the efficient introduction of the aryl group. This intermediate forms a stable bond with the aryl group during the second step, ensuring high reliability and efficiency of the aryl group introduction reaction.
4Productivity
If the reaction of introducing sec-butyllithium is performed by the method in Non-Patent Document 3, then the triorganosilane compound can be produced, but the reaction is low yield
Solution Approach 1:
The invention changes the reaction parameters by using a two-step process where the first step forms the monolithium intermediate and the second step introduces the sec-butyl group via alkylation with sec-butyl halide. This parameter change improves the yield to 80-90% while maintaining reasonable reaction conditions, making the process more manufacturable.
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 method enhances the yield and efficiency of triorganosilane production, avoiding undesired isomers and reducing the need for high temperatures, thereby improving the overall production process.
Implementation Method 1
reacting a diorganosilane compound represented by the formula (I) with a triflating reagent to obtain a monotriflate compound
Implementation Method 2
reacting the monotriflate compound obtained in the step (1) with a metal reagent represented by R3Li or R3MgX to obtain a triorganosilane compound
Implementation Method 3
converting the aryl group into a cycloalkyl group by reacting with hydrogen in the presence of a metal catalyst
Data Source
AI summary
The invention provides a method for producing a triorganosilane compound which includes (1) a step of reacting a diorganosilane compound represented by the formula (I):with a triflating reagent to obtain a monotriflate compound represented by the formula (III):and(2) a step of reacting the monotriflate compound obtained in the step (1) with a metal reagent represented by R3Li or R3MgX to obtain a triorganosilane compound represented by the formula (II):wherein R1, R2 and R3 are as defined herein.