Presentation Title

One Step Synthesis of 4-Trifluoromethylstyrene by Palladium Catalyzed Coupling of Vinyltrimethoxysilane

Abstract

The research project is an organic/polymer chemistry research project based on producing a synthesis of 4-trifluoromethyl styrene in a single high-yield step. Fluorinated polymers are important due to their interesting properties of thermal stability, resistance to weathering, as well as it calls for easy processing. Polymers and copolymers based on 4-pentafluoro sulfuryl styrene are thus important to consider in applications and use, due to their significant properties. Synthetic precursors to 4-pentafluorosulfurylstyrene are quite expensive, therefore a high yielding single step route is desirable. We are attempting to develop this synthetic route using less expensive precursors based on the trifluoromethyl group, specifically 4-bromotrifluroromethylbenzene.

The goal of our proposed research is to develop a relatively low cost, high yielding synthetic route to 4-trifluoromethylstyrene. This polymer when produced in high yield will be able to provide further exploration for new polymer structures based on 4-pentafluorosulfurylstyrene and will be used to compare properties with sulfuryl pentafluoro polymers. A search of the literature shows that coupling alkoxyvinylsilanes via palladium catalyzed reaction may yield promising results. Based on the literature, we are going to attempt traditional synthesis of this key intermediate from 4-bromothiophene.

College

College of Science & Engineering

Department

Chemistry

Location

Winona, Minnesota

Breakout Room

35

Start Date

4-14-2021 3:00 PM

End Date

4-14-2021 3:45 PM

Presentation Type

PowerPoint (pptx, ppt, or PDF)

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Apr 14th, 3:00 PM Apr 14th, 3:45 PM

One Step Synthesis of 4-Trifluoromethylstyrene by Palladium Catalyzed Coupling of Vinyltrimethoxysilane

Winona, Minnesota

The research project is an organic/polymer chemistry research project based on producing a synthesis of 4-trifluoromethyl styrene in a single high-yield step. Fluorinated polymers are important due to their interesting properties of thermal stability, resistance to weathering, as well as it calls for easy processing. Polymers and copolymers based on 4-pentafluoro sulfuryl styrene are thus important to consider in applications and use, due to their significant properties. Synthetic precursors to 4-pentafluorosulfurylstyrene are quite expensive, therefore a high yielding single step route is desirable. We are attempting to develop this synthetic route using less expensive precursors based on the trifluoromethyl group, specifically 4-bromotrifluroromethylbenzene.

The goal of our proposed research is to develop a relatively low cost, high yielding synthetic route to 4-trifluoromethylstyrene. This polymer when produced in high yield will be able to provide further exploration for new polymer structures based on 4-pentafluorosulfurylstyrene and will be used to compare properties with sulfuryl pentafluoro polymers. A search of the literature shows that coupling alkoxyvinylsilanes via palladium catalyzed reaction may yield promising results. Based on the literature, we are going to attempt traditional synthesis of this key intermediate from 4-bromothiophene.