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Chemistry Special Seminar - Dr. Travis Dudding

Posted on 2018-05-25 in Events
Jun 15, 2018

Title: From Proton Sponges and NI-Centered Cations to Au(I) Catalysis


The development of a class of super basic cyclopropenimine functionalized “proton sponge” derivatives, such as DACN (1) andJanus” sponge (2) will be presented. Notably, the strong proton affinity of these bases (PA = 23.8 - 27.0) derives in large part from the generation of aromaticity upon protonation. Going further, several derivatives, e.g., 2, fluoresce both in solution and the solid state, thus making them the first cyclopropenimine-based fluorescent organic compounds. The synthesis and use of cyclopropeniums as phase-transfer catalysts (PTCs) is another topic that will be presented. To this effect, their use in benzylation, fluorination, and O-silyl ether deprotection reactions will be covered. The development of a solid, bench-stable cyclopropenimine containing strong organic Brønsted acid 3 and its use as a catalyst for intermolecular hydroamination reactions of unactivated alkenes and as an activator for Au(I)-catalyzed alkyne hydroamination will also be described. Lastly, the synthesis and application of Au(I)-precatalyst 4 in hydroamination reactions will be presented.

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