Organic Chemistry Seminar

Boryl radical reactivity. Amine-ligated boryl radicals are highly reactive open-shell intermediates with significant potential for the synthesis of borylated materials. In this presentation, I will highlight the use of these species for the C(sp2)–H borylation of azines (e.g., pyridine, quinoline) at positions that are inaccessible via conventional C–H activation methods.[1] Additionally, I will discuss their reactivity with alkenes to form sp3-hybridized materials.[2] These unique reactivities have led to the development of novel, stable borylated materials with a strong capacity to participate in Suzuki-Miyaura cross-coupling reactions. Furthermore, I will present our recent work demonstrating the ability of amine-ligated boryl radicals to activate organic halides via halogen-atom transfer (XAT), and how this strategy can be integrated with nickel and copper catalysis for broader couplings involving aryl halides, aryl boronic acids, and amides.[3]

Photoexcited nitroarenes. Nitroaromatics are widely available feedstocks that are routinely used for the preparation of anilines upon reduction. I will present our most recent work that demonstrates how these species can be used, upon blue light irradiation, to promote the ozonolysis-style cleave of olefins[4] and also allow preparation of complex and highly functionalised saturated heterocycles.[5] Furthermore, I will present our recent work where modulation of the excited configuration of these species has enabled the currently elusive ozonolysis of aromatics in the presence of olefins.