School of Science Department of Chemistry 7 Data Analytics of Homogeneous Transition Metal Catalyzed Reactions Supervisor: SU Haibin / CHEM Student: WANG Yizhou / CHEM Course: UROP3100, Summer Coupling reaction is a significant type of reactions in organic synthesis. In the past decades, researchers have found many transition metals that are able to catalyze various kinds of coupling reactions. As a cheap transition metal, nickel is thought to be an excellent metal to effectively catalyze coupling reactions, and many groups have made a lot of experiments and data about nickel catalyzed C-O activation reactions. This report will try to review different C-O activation reactions catalyzed by nickel and give some characteristics or rules about this reaction field. Development of New Catalytic Organic Processes Supervisor: SUN Jianwei / CHEM Student: HO Hang Chi / CHEM Course: UROP1100, Spring Synthetic organic chemistry is commonly used to synthesize important molecules in our daily lives such as drug molecules and pharmaceuticals. However, many of these molecules contain a chiral carbon atom and have two non-superimposable mirror images, or enantiomers, which can have vastly different biological activity. Therefore, reactions that can preferentially form one enantiomer over the other has seen rapid development in the past century precisely because of its applications in the pharmaceutical industry. Such asymmetric reactions can be catalyzed by either enzymes, transition metal complexes, or organocatalysts. Development of New Catalytic Organic Processes Supervisor: SUN Jianwei / CHEM Student: LI Yuxuan / CHEM Course: UROP1100, Fall Based on preceding results, further optimization of catalytic enantioselective 1,6-addition of 5-methide-5Hindoles, which are generated in situ from dehydration of corresponding indolyl alcohols, has been attempted. Starting from modification on structures of the substrates, different chiral phosphoric acids were used to catalyze the reaction. With the result of catalysts screening in hand, evaluation of common solvents, concentration of reactants, and temperature has been performed. As a continuation of the previous project, this work successfully enhanced the enantioselectivity of the reaction (ee value up to 78%). Although the enantioselectivity of such reaction mode requires further enhancement, the increase in ee value could still prove that optimization on the reaction is effective.