Graduate Program

Chemistry

Degree Name

Master of Science (MS)

Semester of Degree Completion

Spring 2022

Thesis Director

Hongshan He

Thesis Committee Member

Radu F. Semeniuc

Thesis Committee Member

Zhiqing Yan

Thesis Committee Member

Michael W. Beck

Abstract

Heck C-C cross-coupling reaction has been widely employed in synthetic organic chemistry because of its high efficiency and simplicity, however the conventional Heck C-C cross-coupling reaction conditions involve the use of an expensive toxicant phosphine-ligated palladium complexes, and high temperature. To address these drawbacks, a highly efficient, homogeneous photocatalyst based on BODIPY for the Heck C-C cross-coupling reactions of aryl iodide and methyl acrylate in DMF solvent under inert conditions has been developed. The 4-Py-BDP-Pd, 3-Py-BDP-Pd and, 2-Py-BOD-Pd catalysts were synthesized and purified using column chromatography. The optical properties of products and intermediates were studied by UV/vis absorption and fluorescence spectroscopy. Catalysts were used for the C-C cross-coupling reaction between iodobenzene and methyl acrylate which successfully produced a substituted alkene with high reactivities under mild condition. Heck cross-coupling reactions of a wide range of iodobenzene with methyl acrylate have been done to evaluate the substrate scope of the photocatalyzed Heck C-C cross-couplings reactions. When electron donating groups derivatives were used, desired product yields were higher than that of the model reaction. Meanwhile, lower yields were obtained when electron withdrawing groups were used.

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