Manganese-Catalyzed Mukaiyama Hydration Reaction for Undergraduate Organic Chemistry Course

The hydration of olefins is a crucial method in the synthesis of alcohols. Compared to the conventional acid catalysis, oxymercuration/demercuration, and hydroboration/oxidation methods, the Mukaiyama hydration reaction has garnered significant attention in the realm of organic synthesis owing to its merits that encompass mild reaction conditions, easy operational procedures, and the use of a low-toxicity catalyst. However, this reaction has rarely been mentioned in undergraduate textbooks and has not yet been incorporated into laboratory teaching curricula. Here, an experiment is described that includes manganese-catalyzed Mukaiyama hydration of but-3-ene-1,1-diyldibenzene, which is targeted at third-year undergraduates. This process involves utilizing thin layer chromatography (TLC) to monitor the progress of the reaction, isolating the target product through column chromatography, and analyzing the product using 1H nuclear magnetic resonance (NMR) technology. This experiment not only enables students to master the skills of performing the Mukaiyama hydration reaction but also stimulates their interest in organic chemistry, laying a solid foundation for their future scientific research endeavors.