Training Undergraduate Sophomore or Junior Students in Air- and Moisture-Sensitive Reaction Techniques through a Multistep Synthesis of the Tripodal Bis[2-(2,3-dihydroxyphenyl)-6-pyridylmethyl](2-pyridylmethyl)amine (BCATTPA) Compound

Abstract

Many of the current synthetic methodologies utilized within academic and industrial laboratories require knowledge of how to safely handle air- and moisture-sensitive reagents and work under inert atmospheres. As a result, the ACS Committee on Professional Training recommends incorporating synthetic methods that make use of these inert atmospheres into curricula for the development of students with career aspirations in science. However, incorporation of these methods into the curricula at primarily undergraduate institutions is challenging due to access to limited resources and infrastructure. This article reports a semester long, multistep laboratory synthesis of the tripodal bis[2-(2,3-dihydroxyphenyl)-6-pyridylmethyl](2-pyridylmethyl)amine (BCATTPA) compound involving metal halogen exchange, chlorine transfer, nucleophilic substitution, Suzuki cross-coupling, and Lewis acid dealkylation steps that was successfully carried out by sophomore or junior undergraduate researchers enrolled in a Mentored Research in Chemistry course at Fairleigh Dickinson University. Using routine laboratory characterization techniques such as 1H NMR and FT-IR spectroscopies as well as GC-MS, students were able to identify and assess the purities of their resulting products. The disclosed laboratory synthesis enabled students to get formal training in air- and moisture-free Schlenk-line techniques such as syringe and cannula transfers in a controlled learning environment that they could use in future research activities in organic, inorganic, analytical, physical, or biochemistry laboratories.

Rapid Amide Coupling in Water for Undergraduate Laboratories

“…20,25 However, while covering sustainable chemistry topics, the curriculum should not be restricted only to the textbook; the laboratories and lectures must be synchronized. 13,18,19,26,27 During the execution of such new experiments, students get the opportunity to learn about the harmful impacts of traditional organic synthesis while understanding the need to replace outdated experiments. Other advantages of promoting sustainable chemistry practices include the minimization of potential chemical accidents and release of toxic volatiles while ensuring student safety.…”

“…These resources cover broader topics to promote green chemistry in higher education. − Likewise, the Beyond Benign organization also provides resources to educators and students to equip them with tools to practice sustainability. − These tools are helpful in fostering awareness about the environmental impacts of chemistry among students. Despite the availability of these resources and tools, the implementation of greener synthetic protocols in teaching laboratories is still limited. ,− Predominantly, teaching laboratories still rely on the old curriculum, which includes traditional organic synthesis accompanied by longer reaction times and followed by reaction workup, isolation, purification, and analysis of the desired compounds. ,, Often, the entire process consumes more than one lab session, i.e., >4 h. Moreover, it often involves water- or air-sensitive reagents and toxic organic solvents as a reaction medium and for product extraction and purification. Also, the assessment of waste generation from the synthetic pathway is not often used as a learning tool for students. ,, …”

“…The role of organic chemistry instructors is crucial for incorporating newer concepts of sustainable chemistry while designing an effective curriculum. Ideally, interactive discussions among the students and careful textbook selection can give students a broader picture of the importance of the topic. , However, while covering sustainable chemistry topics, the curriculum should not be restricted only to the textbook; the laboratories and lectures must be synchronized. ,,,, During the execution of such new experiments, students get the opportunity to learn about the harmful impacts of traditional organic synthesis while understanding the need to replace outdated experiments. Other advantages of promoting sustainable chemistry practices include the minimization of potential chemical accidents and release of toxic volatiles while ensuring student safety.…”