Cross-coupling reactions have revolutionized the way we approach organic synthesis. While traditional methods focus on aryl and alkenyl halides, recent methods have expanded to include alkyl halides and pseudohalides. My Ph.D. and postdoctoral studies have focused on expanding the limit of reactivity in cross-coupling reactions to include activation of C�O and C�H bonds. The following studies will be highlighted:(1) In the Jarvo lab at UCI, we have developed stereospecific cross-coupling reactions of benzylic ethers, and applied this methodology to the asymmetric synthesis of diarylethanes and triarylmethanes.(2) We have studied the mechanism of this cross-coupling reaction to understand the stereochemistry and how methyl ethers are activated for cross-coupling.(3) In the Houk group at UCLA, we have conducted a DFT study of the mechanism of template-directed C�H olefination reactions developed in the Yu lab (TSRI). We have found that template conformation and distortion orchestrates the unprecedented meta-selectivity.(4) We have developed a method to design new templates computationally to extend meta-selective C�H functionalization to new substrate classes.In the future, my research program will involve undergraduate students in both computational and experimental organometallic chemistry. My students and I will develop a more rigorous understanding of the factors that control cross-coupling reactions at sp3-centers, including the elementary steps of oxidative addition, transmetalation, and beta-hydride elimination. Computational ligand design and experimental validation will also be a key part of my research program.

Cross-coupling reactions: Method development, mechanistic studies, and computational design

248th National Meeting (2014)

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