Title: Simple-Looking but Non-Obvious Transformations
Abstract: Late-stage functionalization has become an increasingly important strategy for increasing structural diversity of analogues in drug discovery. However, the current late-stage functionalization tactics remain limited, mostly centered on C-H functionalization. In this talk, three simple-looking but non-obvious transformations will be discussed, which allow for unusual late-stage modifications of complex molecules. The first transformation promotes directed saturation of unactivated arenes, leading to site-selective conversion of a benzene ring into a cyclohexane ring in complex molecules.1 The second transformation enables simultaneous installation of two chemically different boryl groups side-by-side into common aryl triflates or chlorides, resulting in divergent regioselective difunctionalization.2 The third one represents an “atom swap” strategy, which replaces a carbonyl group with a heteroatom, such as sulfur or nitrogen.3 This method can efficiently introduce saturated heterocycles from readily available cyclic ketones, and the application includes rapid conversion of readily available steroids into the corresponding thia- and azasteroids.
Bio: Guangbin Dong is the Weldon G. Brown Professor of the Chemistry Department at the University of Chicago. After receiving a B.S. degree from Peking University, he completed his Ph.D. degree in chemistry at Stanford University with Professor Barry M. Trost, where he was a Larry Yung Stanford Graduate fellow. In 2009, he began to research with Professor Robert H. Grubbs at California Institute of Technology, as a Camille and Henry Dreyfus Environmental Chemistry Fellow. In 2011, he joined the department of chemistry and biochemistry at the University of Texas at Austin as an assistant professor and a CPRIT Scholar. In 2016, he became a Professor of Chemistry at the University of Chicago. Since 2023, he has been the first chair of the Weldon G. Brown Professorship.
His current research interests include activation of inert bonds, total synthesis of bioactive natural products, boron chemistry, and graphene nanoribbons. For example, his team explores catalytic C-C bond activation as a useful tool for constructing or modifying complex molecular skeletons. Additionally, he is a leading contributor to the palladium/norbornene catalysis, which enables site-selective arene functionalizations and carbonyl transposition. Moreover, his team has invented new activation modes for functionalizing C-H bonds of carbonyl compounds. Finally, his work in boron chemistry enables skeletal modification of heterocycles, efficient preparation of azaborines, and programmable organic synthesis.
Dr. Dong’s Ph.D. research studies involved development of new catalytic enantioselective synthetic methods and applied these methods in the total syntheses of biologically important molecules. The majority of the natural products Dr. Dong synthesized exhibit high potent anticancer activity, such as agelastatin A, terpestacin, and bryostatins. In addition, he has designed and synthesized a new bryostatin analogue; in collaboration with Genetech, this agent has shown nanomolar anticancer activity again several cancer cell lines. This work has been published in Nature.
At California Institute of Technology, Dr. Dong was a Camille and Henry Dreyfus Environmental Chemistry Fellow in the group of Professor Robert H. Grubbs. His research aimed at development of catalysts for anti-Markovnikov hydration of olefins, considered as one of the top 10 challenges in catalysis. Dr. Dong developed the first reproducible anti-Markovnikov olefin hydration process using a dual-metal system.
Dr. Dong’s primary goal as an advisor is to give graduate students and postdocs with professional training that will assist them for their future careers as independent researchers. He will create a healthy environment where both students and postdocs are able to share experiences and knowledge with each other. The key is to offer each group member sufficient freedom to explore on his/her own. They should be allowed to make their own mistakes and correct themselves by finding their own solutions. They will be encouraged to talk more to each other and learn from each other. Meanwhile, he will be around and ready to give suggestions. Dr. Dong believes that such a collaborative environment would be beneficial for students and postdocs to develop into thoughtful scientists capable of conducting research on an independent level.
Hosts: Peter Verardi and Adrian Matthews