This in-class activity introduces students to copper-mediated cross coupling reactions. In the literature, many cross coupling reactions are often discussed using palladium as a catalyst, not copper. In my laboratory, we are synthesizing 7-azaindole-based ligands for the development of potential anti-tumor platinum(II) complexes. In addition, I use one of my own publications to demonstrate an application of this synthetic strategy. The students calculate the actual turnover number (TON) and turnover frequency (TOF) for the copper catalyst.
1) A student will conduct a literature search to gain background knowledge on the Ullmann-type reactions.
2) A student shoud be able to apply their knowledge on Ullmann-type reactions and evaluate the role of each reagent in a given reaction.
3) A student will evaluate the efficiency of a given copper catalyst by calculating TON and TOF.
4) A student should be able to draw a general catalytic cycle for the Ullman-type reaction.
5) A student should be able to identify criteria for a 'mild' reaction.
Chalk board and/or powerpoint
There are various strategies to implement this activity. After a general overview/lecture focused on the fundamentals of catalysis, the students will complete part 1 listed on the activity. The students will conduct a literature search on the Ullmann reaction outside of class and complete the questions. During the following class period, we would discuss their answers to the questions for part 1. The second part of the activity focuses on a literature discussion. The students will be required to read the publication by the Collins research group and answer the questions for part 2 of the activity. We would discuss their answers as a group during the following class period.
The instructor should provide student feedback based on various areas such as level of preparedness and level of knowledge demonstrated. On problem 4, the goal is for the students to think about possible "criteria" for a mild reaction (i.e. lower temperature, low pressure). They should also recognize steps within the catalytic cycle (e.g. oxidative addition, reduction elimination). Moreover, the students should be able to have a discussion about the importance and significance of these types of cross-coupling reactions.