Organic Chemistry Seminar: Designing, Understanding, and Manipulating Radical Reaction Pathways Driven by Light

Hutchison Hall — Rochester, NY

📅Fri, Sep 11, 2026 · 🕐9:00AM – 10:00AM

Join us to hear from Jeffrey Lipshultz about his research at Stony Brook University! Abstract: Efforts in the Lipshultz Group are largely geared towards developing versatile platforms for synthetic transformations, leveraging radical reaction pathways driven by light. Among these platforms are (i) titanium ligand-to-metal charge-transfer (LMCT) photocatalysis, (ii) Vit B6-inspired Photo-Decarboxylase catalysis, and (iii) Vit B6-dependent aminomutase-inspired amino acid homologation. Each of these reaction classes leverages unique photochemical and/or radical key steps which provide opportunity for manipulation and control through fundamental understanding. First, electronic tuning of photoactive titanium catalysts allows for rational manipulation of photochemistry, manifesting in controlled photocatalysis for C–C and C–H bond functionalization. Tuning of the redox properties can further enable reversible C–C bond activation for formal alcohol metathesis. Second, taking inspiration from Dunathan's stereoelectronic hypothesis for Vit B6-dependent enzymatic reactivity, Photo-Decarboxylase catalysis is realized through catalyst-templated hyperconjugative charge-transfer, delivering access to decarboxylated diradical species which engage in regiospecific bond construction. Finally, α-to-β amino acid homologative transmutation can be achieved through a highly polarized biomimetic 3-exo-trig radical cascade. Fundamental mechanistic studies, combined with density functional theory calculations, deliver deeper understanding of these key steps and provide prospects for further development. Host: Rose Kennedy | c.r.kennedy@rochester.edu See our other upcoming seminars here: https://www.sas.rochester.edu/chm/news-events/events/seminars.html