Catalytic Transfer Reactions of Non-Stabilized Carbenes
日期：2024/6/18 15:00
演講者：Prof. Christopher Uyeda
講者現職：Purdue University
主持人：林裕川 教授
地點：四樓創意講堂
語系：English
Carbenes are versatile reactive intermediates that display orthogonal reactivity to common nucleophilic and electrophilic functional groups. Catalytic carbene transfer reactions were first discovered over a century ago, and numerous examples of [n + 1]-cycloaddition reactions have since been developed, often with control over diastereo- and enanatioselectivity. Most of these reactions rely on the controlled decomposition of diazoalkanes as a central strategy to access reactive carbene equivalents.
Despite the utility of diazoalkanes in organic synthesis, they are inherently limited by the need for stabilizing substituents such as aryl or carbonyl groups. In order to develop transfer reactions of nonstabilized carbenes, it is necessary to consider an alternative set of precursors. Our group has shown that nickel and cobalt catalysts can promote reductive [n + 1]-cycloaddition reactions using readily available and indefinitely stable 1,1-dichloroalkanes and 1,1-dichloroalkenes as precusors for carbenes and vinylidenes, respectively. In this seminar, I will describe our development of new cycloaddition methods and our current hypotheses about the mechanisms of these reactions.
Chris Uyeda is the Herbert C. Brown Professor of Chemistry at Purdue University. After growing up in Vancouver, Canada, he attended Columbia University, where he earned his B.S. in biomedical engineering in 2005. As an undergraduate student, Chris carried out research on hydrophobically directed reactions with Prof. Ronald Breslow. Chris then moved to Harvard University to pursue graduate research under the supervision of Prof. Eric Jacobsen. He obtained his Ph.D. in 2011, and his thesis described the development of catalytic enantioselective Claisen rearrangements using chiral hydrogen bond donors. Chris then carried out postdoctoral research with Prof. Jonas Peters at Caltech as an NSF CCI Fellow. His work involved studying electrocatalysts for the production of solar fuels. In 2013, Chris started his independent career at Purdue University. His research program currently focuses on studying catalytic reactions at metal–metal bonds, discovering new catalytic carbene transfer reactions, and synthesizing conjugated materials containing N=N bonds.