CAREER: Harnessing Nitrogen-Heteroatom Bonds for Unsaturated Carbon-Carbon Bond Difunctionalization

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With this CAREER Award, the Chemical Synthesis Program supports fundamental research to be carried out by Professor Qiu Wang at Duke University. Professor Wang will develop new synthetic routes to organic compounds that contain nitrogen. Organonitrogen compounds are widely distributed in nature and they display a broad range of biological activities. Efficient multistep processes are being developed to construct carbon-nitrogen bonds through the use of versatile intermediates. In addition to applications in biological and chemical science, this research has the potential to impact the pharmaceutical, chemical and agricultural industries through the creation of efficient routes leading from readily available starting materials to important nitrogen-containing synthetic intermediates. This research aims to provide broadly applicable strategies for the synthesis of more complex organic structures. To motivate young minds, Professor Wang will develop a training foundation directed at involving women and underrepresented minority students in cutting-edge chemical research. This educational program will encourage students to think creatively and collaboratively, building the skills necessary to undertake complex scientific and social challenges and encouraging students to pursue careers in scientific discovery. Toward this goal, Professor Wang will work with North Carolina local high schools and the Duke Service-Learning Program to provide opportunities for high school students to conduct hands-on experiments at the frontiers of chemistry research. This outreach program will recruit faculty, graduate students and undergraduate students as science ambassadors to visit local schools and to speak on their research. Professor Wang's research focuses on the direct introduction of 1,2-diamino-functionality onto diverse unsaturated carbon-carbon bonds. The project involves the study of reactivity in reagents bearing nitrogen-heteroatom bonds (N-X; X=Cl, Br, I, OR) with the goal of developing operationally simple and efficient amino-functionalization reactions, including (1) the amino-halogenation of arynes to prepare ortho-functionalized aminoarenes, (2) intramolecular amino-fluorination to prepare fluorinated aza-heterocycles, and (3) intra- and intermolecular alkene diamination reactions designed to prepare valuable vicinal diamines. Experimental studies are planned to provide insight into the mechanism and stereochemical outcome of these reactions, potentially guiding the design of second generation N-X to N-C transformations.