Resumen de Experimenting with a Suzuki–Miyaura Cross-Coupling Reaction That Demonstrates Tolerance toward Aldehyde Groups To Teach Undergraduate Students the Fundamentals of Transition-Metal-Catalyzed Reactions
Jie Dai, Dadong Lu, Tao Ye, Shouyun Yu, Xu Cheng
The Suzuki–Miyaura cross-coupling reaction, which is one of the most important methods for C–C bond formation in modern organic synthesis, exhibits broad functional group compatibility. A Suzuki–Miyaura cross-coupling protocol is reported that is suitable for demonstrating this compatibility in undergraduate laboratories. In this reaction, two unique features of boron reagents (tolerance toward water and electrophilic functional groups and reactivity toward transition metal complexes) are well reproduced. Nearly complete conversion of an aldehyde-bearing substrate occurs within 50 min, and the workup and purification procedures are convenient. The reaction was readily reproducible by second-year students in a first-semester undergraduate laboratory.
