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Abstract
Nitroalkenes are versatile intermediates in organic synthesis, playing a crucial role in pharmaceutical and material science applications. Existing synthetic methods often suffer from low efficiency, necessitating the development of a more reliable and scalable approach. This study presents a novel strategy for the Saegusa–Ito-type desaturation of nitroalkanes, utilizing sequential electrochemical oxidation and photochemical elimination. The transformation proceeds via an α-iodo nitroalkane intermediate, generated through oxidative coupling with sodium iodide, followed by photochemical activation to afford the desired nitroalkene. Current efforts focus on optimizing reaction yields, and future studies will investigate the reaction mechanism using NMR, cyclic voltammetry (CV), electron paramagnetic resonance (EPR), and density functional theory (DFT) calculations. This study represents a significant advancement in nitroalkene synthesis, providing a robust and scalable method with broad applicability in organic chemistry.
Home Country
United States
College
College of Arts & Sciences
Specialization
Chemistry
Faculty Sponsor
Minsoo Ju
Presentation Type
Event
Saegusa–Ito Oxidation of Nitroalkanes Enabled by Sequential Electrochemical Oxidation and Photochemical Elimination
Nitroalkenes are versatile intermediates in organic synthesis, playing a crucial role in pharmaceutical and material science applications. Existing synthetic methods often suffer from low efficiency, necessitating the development of a more reliable and scalable approach. This study presents a novel strategy for the Saegusa–Ito-type desaturation of nitroalkanes, utilizing sequential electrochemical oxidation and photochemical elimination. The transformation proceeds via an α-iodo nitroalkane intermediate, generated through oxidative coupling with sodium iodide, followed by photochemical activation to afford the desired nitroalkene. Current efforts focus on optimizing reaction yields, and future studies will investigate the reaction mechanism using NMR, cyclic voltammetry (CV), electron paramagnetic resonance (EPR), and density functional theory (DFT) calculations. This study represents a significant advancement in nitroalkene synthesis, providing a robust and scalable method with broad applicability in organic chemistry.
