Melissa Ashley, Rovis Group
10:00am - 11:00am
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Given the prevalence of primary amines in biologically active molecules, an important area of research is devoted to creating methods to site-selectively functionalize their C(sp3)-H bonds. For simple aliphatic primary amines, many of these C-H bonds are chemically indistinguishable due to their similar electronics and sometimes, steric environments. Through strategic choice of activating group, site-selective functionalization at both a– and d– positions is achieved. Exploiting inductive effect allows for a photoredox-catalyzed a-C(sp3)-H alkylation of trifluoromethanesulfonamides. In the case of trifluoroacetamides, functionalization is directed to a distal C(sp3)-H site via [1,5]-hydrogen atom transfer which results in a formal d-aminomethylation and d-cyanation. Lastly, by subjecting primary amines to an electron-rich benzaldehyde activating group, we leverage C-N bonds as a functional handle for deaminative radical cross-couplings.
Friday, October 9, 2020 at 10:00am EDT
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