C-H activation reactions are reactions in which a carbon-hydrogen bond is directly functionalized. These reactions improve the efficiency of obtaining a desired product by eliminating several intermediate reactions. Catalytic C-H activation of weak carbon-hydrogen bonds in 1,2,3,4-tetrahydronaphthalene (tetralin) to form C=O and C-OH bonds was observed to occur in the presence of iodosylbenzene (PhIO) – an oxidant, and N-hydroxyphthalimide (NHPI) – the catalyst. The amount of PhIO and NHPI were varied to optimize the reaction to produce the greatest amount of 1-tetralone. Other parameters such as solvent, temperature, time, and control reactions were also conducted to optimize the reaction conditions for the production of 1-tetralone. Through the control reactions, it is clear that both NHPI and PhIO must be present in the reaction mixture for the C-H activation reaction to occur. The reaction also was determined to produce the best yields of 1-tetralone using d-chloroform (0.1 M), 1.2 equivalents of PhIO, and 30 mol % of the catalyst NHPI. Analysis of the products of the reaction indicates that several NHPI derivatives are formed during the course of the reaction which are not reactive intermediates; these products could be a reason for the incomplete conversion of tetralin to 1-tetralone. In future reactions we would like to avoid or slow the formation of these products to attempt to gain better yields of 1-tetralone.

Sravya Ainapurapu would like to thank their faculty sponsor Jamie Neely for their support of this project.