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Marcus Mifflin Ogden, UT.

Chemistry

Leadership Track

WMG Research Fellowship

The Walter Maxwell Gibson Research endowment is awarded to students within the College of Science and Engineering for fellowships to conduct research for projects that make an intellectual or creative contribution to an area of study within the college. I spent the summer working full time on a research project, and the endowment provided 300 hours of paid time for this work. For my project, I conducted an organic chemistry research study under the supervision of Dr. Nathan Werner in which I synthesized a pinacolborane substituted diene by the 9-BBN catalyzed hydroboration of the enyne (E)-but-1-en-3-yn-1-ylbenzene (fig 1). The production of organoboronic ester derivatives is becoming increasingly important in modern organic synthesis due to their versatility in forming C-C bonds by Suzuki-Miyaura cross-coupling reactions. Suzuki-Miyaura cross-coupling reactions are valuable tools that synthetic chemists use when building large complicated molecules, and they’re commonly

used in the synthesis of many important and widely prescribed medications.

Organoborane molecules are typically produced by the anti-Markovnikov hydroboration reaction of alkenes or alkynes. We were interested in the selectivity of the hydroboration reaction when both an alkene and alkyne are present in the same molecule. We hypothesized that the more electron-rich alkyne will preferentially react in this situation. This would allow for the selective synthesis of borodienes that may also have interesting properties and reactivity. In the end, we were able to successfully achieve the synthesis of the target molecule by the desired reaction, but we were unable to examine the reaction conditions due to complications that arose along the way.

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Fig 1. Final reaction in the synthesis of 4,4,5,5-tetramethyl-2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)-1,3,2-dioxaborolane

The reason I chose to undertake this project is because of my passion for chemistry. I’m planning on attending graduate school for organic chemistry after I graduate which is almost entirely focused on research. We chose this particular synthesis for a couple of reasons. The first of which is because it had never been previously done, and the second is because we want to use the end product in cross-coupling reactions which have not been well studied for this particular molecule. Furthermore, we are also interested in the reactivity of the cross-coupling product, and its potential application in other types of reactions.

Many complications arose throughout the duration of the project. The biggest of which came about from the reaction we used to produce the enyne. Without this reactant we could not test the reaction of interest, and so a great deal of time was spent trying to get the reaction to work efficiently enough to supply us with an adequate amount of the starting material. Many different strategies were employed in an attempt to get around this, but nothing ended up giving the desired results. We concluded that an alternative synthesis of the enyne is needed if we are to continue this research.

I was able to have a direct impact on the other researchers in our lab because of this project. As a senior lab member, I was in many ways responsible for guiding the newer members. This included training them on certain techniques, giving advice on the next steps to take, and helping them to succeed in however I could. This helped to instill a passion and respect for this kind of work for a couple of the members. Additionally, research projects such as these are done to contribute to the global effort of improving humanities accumulative knowledge. The more knowledge that we gain, the better chance we have at tackling the world's problems, which ultimately is a benefit to all of humanity.

This project was a great benefit for me because it has helped prepare me for my future work as a graduate student since I’ll be doing mostly research when I get into graduate school. As such, this project gave me massive insight into the full process that goes into a research project of this type. I’ve enhanced my ability to problem solve and troubleshoot when things go awry. Additionally, it allowed me to practice many of the techniques and skills that are routinely used in the field. My leadership skills have also improved because I was constantly teaching and guiding the newer members. The picture below shows my mentor, several other group members and I at our annual end of summer barbecue.

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Fig 2. From left Hayden Bishop, J. Brenton Bushnell, Marcus Mifflin, Garett Ruesch, Nathan Werner.

“Even after finishing up for the day, I constantly find myself thinking about what I can do to get things to work the way I want them to. Whenever I think of something, it fills me with excitement for the next day that I can try it out.” -Marcus Mifflin