Microwave irradiation is a useful method to heat food and organic reactions. It can provide shorter reaction times and unusual reactivity when compared to traditional, conduction heating on a hotplate. The conduction heated palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (E)-2-phenylethenylboronic acid pinacol ester with aromatic bromides was discovered and developed at SUU. However, the analogous reaction heated by microwave irradiation was unknown. Here, we describe the synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (E)-2-phenylethenylboronic acid pinacol ester with aromatic bromides heated by microwave irradiation. The reaction conditions developed for conduction heating were evaluated for reactions heated by microwave irradiation. Various electronically diverse aromatic bromides were studied in reactions heated by microwave irradiation. The yields and reaction times of reactions heated by microwave irradiation were improved when compared to reactions heated by conduction. Interestingly, the scope of compatible aromatic bromides bearing challenging electron-donating substituents was increased when microwave heating was used.
University / Institution: Southern Utah University
Format: In Person
SESSION B (10:45AM-12:15PM)
Area of Research: Science & Technology
Faculty Mentor: Nathan Werner