Faculty Sponsor(s)
Andrew Baggett
Location
Jereld R. Nicholson Library: Grand Avenue
Subject Area
Chemistry
Description
This project optimizes a reaction that uses boron substrates and copper to form sp3-sp3 carbon-carbon bonds. This research project had three main goals: to develop a GC (gas chromatography) method that would allow us to calculate how much of the final product was formed, to optimize the model reaction, and to explore the diversity of other boron substrates that could be used. Working with the GC involved trouble shooting different methods as well as testing our internal standard, cis-decalin, to ensure that the solvent wouldn’t cause any side reactions. Standard curves were created to allow us to calculate how much cis-decalin remained after going through the GC, which in turn would help calculate the percent yield of the molecule with the sp3-sp3 carbon-carbon bond from the model reaction. Many elements of the model reaction were explored, like a change in solvent, temperature, time, molar ration of the reactants, and which copper additive was used. In comparing the results from the GC, we can figure out which of these methods work the best for obtaining the highest yield possible. To determine if this methodology would work for other boron substrates, different substrates must be tested with these conditions. B(dan) was chosen as the next test substrate, as it can be synthesized in lab. Once the B(dan) is synthesized, a Grignard reaction can be used to generate a library of B(dan) substrates.
Recommended Citation
Northrop, Abigail, "Optimization of copper-catalyzed oxidative alkylboron homocoupling" (2022). Linfield University Student Symposium: A Celebration of Scholarship and Creative Achievement. Event. Submission 25.
https://digitalcommons.linfield.edu/symposium/2022/all/25
Optimization of copper-catalyzed oxidative alkylboron homocoupling
Jereld R. Nicholson Library: Grand Avenue
This project optimizes a reaction that uses boron substrates and copper to form sp3-sp3 carbon-carbon bonds. This research project had three main goals: to develop a GC (gas chromatography) method that would allow us to calculate how much of the final product was formed, to optimize the model reaction, and to explore the diversity of other boron substrates that could be used. Working with the GC involved trouble shooting different methods as well as testing our internal standard, cis-decalin, to ensure that the solvent wouldn’t cause any side reactions. Standard curves were created to allow us to calculate how much cis-decalin remained after going through the GC, which in turn would help calculate the percent yield of the molecule with the sp3-sp3 carbon-carbon bond from the model reaction. Many elements of the model reaction were explored, like a change in solvent, temperature, time, molar ration of the reactants, and which copper additive was used. In comparing the results from the GC, we can figure out which of these methods work the best for obtaining the highest yield possible. To determine if this methodology would work for other boron substrates, different substrates must be tested with these conditions. B(dan) was chosen as the next test substrate, as it can be synthesized in lab. Once the B(dan) is synthesized, a Grignard reaction can be used to generate a library of B(dan) substrates.
