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

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.