MAIN-GROUP OXYGEN-ATOM TRANSFER REAGENT: INVESTIGATING µ-OXO-BRIDGED BINUCLEAR COMPOUNDS FOR CATALYTIC OXIDATION REACTIONS

Author

Thien Nguyen, University of Texas at ArlingtonFollow

ORCID Identifier(s)

ORCID 0009-0008-8750-3765

Graduation Semester and Year

Spring 2025

Language

English

Document Type

Thesis

Degree Name

Master of Science in Chemistry

Department

Chemistry and Biochemistry

First Advisor

Gyeongjin Park

Second Advisor

Rasika Dias

Third Advisor

Fred MacDonnell

Abstract

Oxygen-atom transfer process plays a vital role in both chemical and biological processes. In synthetic chemistry, catalytic oxidation reactions play a crucial role by enabling selective oxygen incorporation into molecules. While transition metals have traditionally been the catalysts of choice, recent developments in main-group chemistry suggest that main group elements, in particular the heavy pnictogen oxides such as antimony oxides, can become a promising alternative. However, monomeric Sb-O or Bi-O bonds pose stabilization and reactivity challenges due to the large atomic orbitals of these heavy pnictogen elements and the notable electronegativity differences between oxygen and the heavy pnictogen elements. To address these concerns, bulky substituents, such as diisopropylphenyl, or Lewis acids, such as tris(pentafluorophenyl) borane, are applied to help stabilize these monomeric heavy pnictogen oxides. Among the stabilized monomeric heavy pnictogen oxides, I propose that (C₆H₅)₃SbOB(C₆F₅)₃ (1), a µ-oxo-bridge binuclear compound, can promote oxygen transfer through a Lewis acid pair interaction mechanism, with the Sb-O-B bridge acting as a stabilizing reactive intermediate. This research first focuses on developing a more efficient synthetic route for compound 1 in the lab. Once obtained, I examine the compound’s electronic structure as well as reactivity, with the focus on proving its oxygen-atom transfer capability. I evaluate it by conducting the reaction of 1 with triphenyl phosphine, while its reversible interaction with water indicates that it remains stable even in previously incompatible conditions. This flexibility creates new pathways to explore its effectiveness across diverse reaction environments. I also look to broaden the potential of main-group-based catalytic systems as visible alternatives to transition-metal catalysts in oxidation reactions, increasing the applications of catalytic oxidation in synthetic chemistry.

License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

Nguyen, Thien, "MAIN-GROUP OXYGEN-ATOM TRANSFER REAGENT: INVESTIGATING µ-OXO-BRIDGED BINUCLEAR COMPOUNDS FOR CATALYTIC OXIDATION REACTIONS" (2025). Chemistry & Biochemistry Theses. 118.
https://mavmatrix.uta.edu/chemistry_theses/118