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.
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