The development of practical and general methods for chemical synthesis enables green and efficient routes to small molecules used in materials science, biology, and medicine with societal impacts beyond the field of organic chemistry. The use of transition metal catalysis has been a particularly effective approach for developing methods for organic synthesis. This research describes a unified and general strategy for oxidation using transition metal catalysis. Undergraduate and graduate students conducting this research learn about developing practical methods, including improving reaction conditions through systematic variation of conditions and detailed investigations into fundamental chemical processes. Student training extends out of the laboratory and into the community, where they learn how to engage K-12 students and excite children's interest in the chemistry of metals.
This research describes the invention of dehydrogenation reactions that use palladium catalysis in conjunction with allyl acetate as an oxidant. This approach fills a long-standing gap in chemical synthesis and avoids the well-recognized drawbacks of previous step-inefficient solutions, such as unstable enoxysilane intermediates, toxic selenium byproducts, or undesirable halogen waste. In addition to the above benefits, the use of a non-electrophilic oxidant, allyl acetate, allows for transformations that tolerate highly oxidation-prone functionality, such as unprotected amines and alcohols, common to bioactive small molecules. Furthermore, these investigations into palladium-catalyzed processes, akin to the Saegusa oxidation, utilize alpha-hydride elimination to effect diverse carbon-carbon bond forming construction reactions. The educational objectives may increase resources available to women at small colleges, through the development of a summer exchange program, and to economically disadvantaged, underrepresented minorities of the New Haven public school system, through creation of short demonstrations and lectures, weeklong mini-courses, academic year laboratory exercises, and summer internships.
