Author(s): David Mefford
Mentor(s): Nathan S. Werner
Institution SUU
Stilbene derivatives are a highly versatile class of compounds that are important to various fields and industries including pharmaceuticals, agriculture, and materials science. These compounds have unique optical, electronic, and biological properties that make them useful in a variety of applications. (E)-Stilbene derivatives can be synthesized using the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (E)-2-phenylethenylboronic acid pinacol ester with aryl bromides. Here we present our study of the pair-wise electronic effects of electron-donating and electron-withdrawing groups of the organometallic donor and organic electrophile on the yield of this reaction. The electron-donating substituents evaluated include a methyl, methoxy, and amine. The electron-withdrawing substituents evaluated include an ester and nitro group. The isolated yields of the cross-coupling product ranged from 39% to 95%.