This Phase I Center will address the foremost challenges in the field of C?H functionalization: the regioselective and stereoselective modification of unsaturated carbon centers. The goal is to make available a suite of chemical transformations for C-C, C-N, C-O, and C-X bond formation that are predictable, general, and utilitarian. The realization of this objective will provide novel technologies that change traditional paradigms for the logic of chemical synthesis.
The Center for Stereoselective C-H Functionalization will broadly share their research results to maximize the impact of this award. The Center will also fund collaborative training opportunities between Center investigators and also with industrial partners for graduate students and postdocs. The Center will partner with regional Minority Serving Institutions (HBCUs or HSIs) to provide symposia and research opportunities to students from under-represented groups. Center investigators will also engage high school teachers and students in the Center projects.
The Centers for Chemical Innovation (CCI) Program supports research centers that can address major, long-term fundamental chemical research challenges that have a high probability of both producing transformative research and leading to innovation. These Centers will attract broad scientific and public interest by sharing the results of their innovative approach to this challenging question.
The goal of the Phase I Center has been to build a community of scholars to take on the multidisciplinary challenges associated with bringing C-H functionalization into the mainstream of organic synthesis. C-H functionalization is a multi-component challenge that requires input from several types of chemists. Traditionally most of the academic efforts on C-H functionalization studies had been focused on developing the reactivity and understanding the chemistry of reactions that will functionalize a C-H bond. Before being in a position to broadly apply C-H functionalization, however, it is necessary to make sure that powerful and practical synthetic methodologies are developed and that these methods can be incorporated into broadly useful synthetic strategies. The Phase I Center was built around experts in C-H functionalization methodology development who also understood synthetic strategy. These were Huw Davies and Simon Blakey from Emory University, Justin Du Bois from Stanford University, Christina White from the University of Illinois, and Jin-Quan Yu from Scripps. The sixth member of the Phase I team was computational chemist, Jamal Musaev. During the Phase I funding period, the Center developed collaborative research amongst the phase I participants and interactions with prospective members for the Phase II Center. This was done through a pilot project solicitation, a C-H functionalization symposium in which potential collaborators were invited, and the initiation of exploratory collaborative research projects. Through this process eighteen additional investigators were recruited, covering the fields of inorganic coordination chemistry, catalyst development, computational chemistry, inorganic and organic mechanistic analysis, total synthesis, biocatalysis, macromolecular catalysis, and chemical engineering. During the phase I studies, the group published a total of 29 papers. Eleven of the publications involved contributions from at least two research groups. The publications were generally in very high tier journals, with 10 publications in the Journal of the American Chemical Society, 3 in Angewandte Chemie and 1 in Nature Chemistry. The collaborative publications included several studies combining theory and experimental studies and others combined physical organic studies and synthetic organic studies. Several projects were initiated and are still in progress where two or more synthetic groups combined resources to tackle challenging problems in C-H functionalization. One project of this type was published and several more are likely to come to fruition in the near future in the phase II Center. Eight of the papers were in the form of reviews, which were directed towards demonstrating the broad synthetic possibilities of C-H functionalization. Yu edited a book on C-H functionalization In Topics of Current Chemistry in 2010 and both Davies and Du Bois contributed chapters to this book. Davies, Du Bois and Yu guest edited a thematic issue on C-H Functionalization in Chemical Society Reviews in 2011 and Davies contributed a tutorial review to this issue. Houk edited an issue of Accounts of Chemical Research in 2012 and Davies, Du Bois and Yu published personalized accounts to this issue. At this stage the Center has already made a considerable impact in the primary literature on C-H functionalization and has contributed greatly to the broader dissemination of how to use C-H functionalization, in the form of reviews and book chapters. The Center has been exploring several new approaches to communicating the excitement of C–H functionalization and the importance of organic synthesis and chemical catalysis. In Phase I, the Center piloted two new courses at Emory, which will form the basis for the creation of workshops and webcasts for all Center members in Phase II: C–H Functionalization and Communicating Science. The Center was also active in the education of undergraduates. In addition to hosting undergraduates for summer and school year research, the Center piloted an undergraduate journal club for Spelman College students, in response to a need by Spelman to better prepare their students for graduate school in chemistry. One of the major challenges of C–H functionalization methodologies is the development of an understanding on the best ways to utilize this chemistry. Therefore, the Center has taken a proactive approach to disseminate this information in the form of reviews, monographs and highlights. Catalyst systems that are being employed within the Center have generated considerable interest in the broader chemical community. In order to ensure that the chemistry is widely accessible, the Center has developed arrangements with the most established chemical suppliers (Aldrich, Acros, Strem) to have the catalysts commercially available. Additionally the Center has developed close ties with pharmaceutical companies because C-H functionalization could have a profound effect on how pharmaceutical drugs are made. These interactions are generating great dividends because it allows the Center to explore "real" problems in addition to the fundamental academic challenges.
