Primary School Student. When you have a cold and want to feel better, you are given cold medicine. That medicine was designed by scientists and that medicine is made to help fight colds. There are different types of medicines to help treat different types of sicknesses. To make those medicines, we need to know how they are put together. Each medicine has its own special shape made from different pieces, and scientists must figure out how to put them together in the correct order. Sometimes, creating a medicine can be expensive or take a lot of time and there could be a better way to make it. You can compare this to going to school. There are probably a few routes to get to your school, but one route could be the easiest and the fastest, so that is the best route. We are helping to try to find the best route to make the kinds of medicine we need, and this could be cheaper, faster and safer for other scientists.

Secondary School Student. When you look at a structure of a drug, there are many different types of bonds, and each drug has its own specific formula. To make these compounds, it usually requires several steps and some of the steps can be expensive, toxic, or harmful to the environment. We are trying new methods that are potentially non-toxic, less expensive, and more environmentally safe, which can help scientists make drugs more easily. Our project focuses on replacing the hydrogen in carbon-hydrogen bonds with a nitrogen to create a carbon-nitrogen bond. Having the ability to add nitrogen to a compound is important because nitrogen is found in natural products, pharmaceuticals, and agricultural products.

College Student. When observing a complex organic molecule, the motif often has different types of C—H bonds, such as primary, secondary, and tertiary, each with distinct reactivity. Having the ability to choose which C—H site to functionalize on a molecule is important. My work focuses on being able to replace the hydrogen in a C—H bond to a nitrogen and generate a C—N bond. Having the ability to add nitrogen to a compound is important because nitrogen atoms introduce unique chemical properties and as a result are found in natural products, pharmaceuticals, and agricultural products. Previous methods to replace hydrogen atoms with nitrogen can sometimes be toxic, expensive, or harmful to the environment. We are experimenting with new methods that are potentially non-toxic, less expensive, and more environmentally safe. With the use of a catalyst and a nitrogen source, we can form C—N bonds on different compounds.  

Graduate Student. When observing a complex organic molecule, the motif often has different types of C—H bonds, such as primary, secondary, and tertiary, each with distinct reactivity. Direct C(sp³)—H functionalization reactions with controlled site selectivity give chemists an opportunity to make novel molecular scaffolds. Amination reactions are generally of interest due to the prevalence of nitrogen-containing motifs in a wide range of relevant compounds such as natural products, pharmaceuticals, and agrochemicals. My research is based on a previous discovery of conditions for organocatalytic C(sp³)—H amination of benzylic positions and aliphatic substrates activated by stereoelectronic effects. This was achieved using the iminium salt organocatalyst in combination with an iminoiodinane nitrene source, although the reaction was slow. By adjusting the structure of the iminoiodinane, which is involved in the rate-determining step of the reaction, I have been able to aminate compounds with faster reaction times. Further, with this newly developed method, I have been able to aminate tertiary benzylic C—H bonds, which was unachievable with the previous reaction conditions. These advances will allow for a wider array of molecules to be functionalized at additional unique positions.

Expert. Having the ability to choose which C—H site to functionalize on a complex molecule is important and direct C(sp³)—H functionalization reactions with controlled site selectivity give chemists this opportunity. In previously published work, intermolecular organocatalytic C(sp³)—H amination of benzylic positions and aliphatic substrates activated by stereoelectronic effects was demonstrated using iminium salt organocatalyst in combination with an iminoiodinane as a nitrene source. The reactions were initially carried out at room temperature over the course of 20 hours. By adjusting the structure of the iminoiodinane, which is involved in the rate-determining step of the reaction, I have been able to aminate compounds with significantly faster reaction times, ranging from 2 to 6 hours. Further, I have also been able to aminate tertiary benzylic C—H bonds with the new iminoiodinane derivatives, which was previously unachievable with the previous reaction conditions. I am currently working on aminating natural products to demonstrate the potential use for this method in late-stage functionalization. The ability of these reaction conditions to modify a variety of unique bonds will make it a powerful tool for drug development and testing.