Introduction of Low-Barrier High-Throughput Experimentation in the Undergraduate Laboratory: Suzuki-Miyaura Reaction

摘要

A contemporary undergraduate laboratory experiment incorporating parallel microscale experimentation was developed for the well-defined palladium catalyzed Suzuki-Miyaura cross coupling of 4-fluorophenylboronic acid with both 4- chloro- and 4-bromoanisole using 11 diverse phosphine ligands and one ligandless control. This laboratory introduces students to low-barrier high-throughput experimentation (HTE) technique that is widely utilized in both academic and industrial research settings. This experiment compliments current topics discussed in organic chemistry, inorganic chemistry, and organometallic chemistry lecture courses and serves to reinforce the students' understanding of fundamental concepts of transition metal mediated cross-coupling reactions. Students are also exposed to common analytical tools (thin layer chromatography (TLC) and high-pressure liquid chromatography (HPLC)) used in research settings to analyze the corresponding experimental data.