Investigation of olefins as a cocatalyst for halonium catalysis

Abstract

Olefins are rarely used as catalysts in chemical reactions. Here, we explore the use of olefins as cocatalysts to facilitate iodonium catalysis. Our catalytic system employs a simple olefin as a cocatalyst with a simple halogen source N-iodosuccinimide (NIS) in hexafluoroisopropanol (HFIP) to form the active iodonium catalyst. Kinetic studies indicate that the olefin cocatalyst structure impacts the reaction rate significantly. In addition, NMR, kinetics, IR and computational studies were incorporated to understand the role of the olefins in these catalytic reactions, opening doors to other potentially interesting catalytic designs.