Scope and utility
The Miyaura-Suzuki cross-coupling reaction (MSC) is a set of conditions that can be used to synthesize poly-olefins (chains of unsaturated hydrocarbons), styrenes, or substituted biphenyls. This reaction is also known as a Suzuki cross-coupling reaction, named after Akira Suzuki, who originally published the reaction in 1979. His work with this reaction allowed him to share the 2010 Nobel Prize in Chemistry with his colleagues. In the scope of this paper, the reaction is used to connect two substituted phenyl groups of the same molecule forming an intramolecular biphenyl. This reaction requires iodine to be present on both of the phenyl groups. It then utilizes a palladium catalyst to complex with the iodine and the ring, and it undergoes a series of substitutions and other reactions with Bis(pinacolato)diboron and Potassium Carbonate. Eventually, the palladium catalyst is the only reactive molecule left, and it connects the two phenyl groups while reverting back to Pd0. Cox et. al. are essentially using the MSC to help re-synthesize Herquline B and C after breaking them apart to simpler compounds. Re-synthesizing these molecules from more commercially available compounds and known technoiques (such as the MSC) is useful as it prevents the need to collect the molecules naturally from fungi secretions. It is also important as Herquline B and C have many practical medical uses for preventing blood clots and fighting influenza. |