Date of Award

2022

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Black, Rebecca

Area of Concentration

Chemistry

Abstract

This thesis describes the synthesis and characterization of a BIPHEP-type (2,2'- Bis(diphenylphosphino)biphenyl) ligand with four pendent ethyl substituents (2-EtBIPHEP, Chapter 2) and efforts toward another BIPHEP-type ligand, 2-COOHBIPHEP, that contains four pendent carboxylic acid substituents (Chapter 4). 2-EtBIPHEP was successfully synthesized at a 1-gram scale over four reaction steps starting from PCl3. Three literature procedures for the synthesis of o-bromooxazoyl benzene (BrPhOx) were tested ; one procedure allowed us to prepare 14.42 g of BrPhOx (84.9% yield). The ability for LiPhOx to react with phosphorous electrophiles was also explored . An initial investigation of the behavior and thermal stability of one Ru complex, [CpRu(2-EtBIPHEP)(MeCN)]PF6, under alcohol acceptorless dehydrogenation conditions is discussed in Chapter 3. The metal complex bearing 2-EtBIPHEP was thermally unstable under catalytic conditions, so the thermal stability of this complex was explored using several solvents, temperatures, and other additives. This work contributes towards an ongoing project using these ligands to investigate the importance of ligand pKa in alcohol acceptorless dehydrogenation.

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