In fall 2012, Professor Neil Garg from University of California-Los Angeles (UCLA) received a $50K grant from the ACS GCI Pharmaceutical Roundtable (ACS GCIPR) Medicinal Chemistry team for his project, “Development of Green Nickel-Catalyzed Cross-Coupling Reactions.” This work was in response to the Roundtable’s call for research on alternatives to precious metals in catalyzed reactions; cross-coupling reactions are critical in industry, as they are one of the most used for assembling carbon-carbon and carbon-heteroatom bonds. Not only did Garg and his team achieve these conditions by replacing typically employed palladium catalysts with lower cost, more abundant nickel-based catalysts, they were able to do so in greener solvents (such as 2-Methyltetrahydrofuran (2-Me-THF), which can be derived from renewable feedstocks).
Fast forward one year later: the team has achieved their goal, having developed a process and delivered an Organic Letters publication, “Nickel-Catalyzed Suzuki-Miyaura Couplings in Green Solvents.” But because a constant objective is to expose students to green chemistry early in the game, the ACS GCIPR and Prof. Garg wanted to take his research a step further. The Roundtable decided to grant an additional $10K in order to have these research developments translated into an undergraduate teaching lab. The extension was an important opportunity for a graduate student to take the lead, so Garg worked with Dr. Jonah Chang (UCLA Lecturer) and Liana Hie (graduate student in the Garg group) to adapt the chemistry for an undergraduate class entitled, “CHEM 144: Practical and Theoretical Introduction to Organic Chemistry.”
After the initial one-year research grant, there were many substrates presented as options and the team had many variations on the process. In order to convert this into a teaching experiment, there was much work to do in terms of optimizing the timing and selecting the most favorable substrates, solvents and catalysts.“We wanted to cover a lot of ground with this lab—we wanted to have the students learn about green chemistry, cross-coupling, heterocycles, metal selection.” Garg explains, “We wanted to teach these things because they are important for pharmaceuticals and are not usually addressed in undergraduate classes, so it’s something new and applicable.”
A student displays his product from the cross-coupling lab with graduate student, Liana Hie.
The team had to work fast in order for the lab to be included in the undergraduate classes this spring; as a result it wasn’t included in the syllabus and was optional for all students in CHEM 144. With green chemistry becoming more prevalent and necessary in academia and industry, and being of great interest to the next generation of chemists, it’s no surprise that the lab was a huge success. There were glowing student reviews of the lab (in the class survey one student relayed "I was surprised to learn [about] the many possible ways to perform green chemistry. This experiment made me think about the option to seek out jobs related to green chemistry.”). Every student participated in this optional exercise, and 29 out of 30 were able to successfully obtain the desired product. “A lot of the standard chemistry curriculum is old… Students were excited to work on something new and that reflected important problems,” Garg explains.
The next goal is to publish the lab experiment and make it more widely available for other universities to employ. Garg emphasizes the importance of building community and taking the initiative as an educator to spread the word about greener lab options. “We’re in the business of education, and we need to align research and education efforts,” says Garg. He hopes to see more efforts like this in the future, both from his lab and others. The ACS GCIPR grants are an effective approach to ensure that academic research and industrial practice coordinate, and as this grant extension exemplifies a key tactic for bringing green chemistry into the classroom.
Commenting on the collaboration the ACS GCIPR states, “While the initial goal of funding this research was to provide a widely applicable method for the catalysis of cross-coupling reactions, which could be applied to industrially relevant substrates, the extension to develop the methodology into a teaching class experiment at UCLA represents a win/win situation on multiple levels for the ACS GCIPR. The experiment developed enables the next generation of scientists to gain experience with a key reaction transformation of significant industrial relevance under environmentally-benign conditions. In addition, we are excited by the results generated while working with Professor Garg, and are grateful for his commitment and engagement throughout the period of research. We also believe that this collaboration will serve as a blueprint in terms of success for future partnerships between academia and the ACS GCIPR”.
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