THE DESIGN AND SYNTHESIS OF NOVEL CHIRAL 2,2’-BIPYRIDINE LIGANDS
| dc.contributor.advisor | Tius, Marcus A. | |
| dc.contributor.author | Liu, Chaolun | |
| dc.contributor.department | Chemistry | |
| dc.date.accessioned | 2024-02-26T20:14:01Z | |
| dc.date.available | 2024-02-26T20:14:01Z | |
| dc.date.issued | 2023 | |
| dc.description.degree | Ph.D. | |
| dc.identifier.uri | https://hdl.handle.net/10125/107900 | |
| dc.subject | Chemistry | |
| dc.subject | bipyridine | |
| dc.subject | catalysis | |
| dc.subject | chiral auxiliary | |
| dc.subject | chiral ligands | |
| dc.subject | cyclopentadiene | |
| dc.subject | ligand design | |
| dc.title | THE DESIGN AND SYNTHESIS OF NOVEL CHIRAL 2,2’-BIPYRIDINE LIGANDS | |
| dc.type | Thesis | |
| dcterms.abstract | Camphor as a chiral starting material has been widely used in the preparation of chiral auxiliaries and asymmetric ligands. Among the variety of applications, the camphor skeleton with pyridine has been a target for the synthesis of chiral bipyridine ligands. The 2,2’-bipyridine ligand is one of the most commonly used ligands in coordination chemistry. Thus, the development of new chiral bipyridine ligands is of great importance in synthetic chemistry. This thesis describes the design and synthesis of a novel tunable camphor-derived chiral 2,2’-bipyridine ligand. Additionally, the progress towards the synthesis of a planar chiral DMAP catalyst will be discussed. In Chapter 1, the use of camphor in the synthesis of asymmetric pyridine ligands is introduced. The -facial selectivity of camphor-derived cyclopentadiene will be described as well. Next, the development, applications, and limitations of chiral 2,2’-bipyridine ligands are discussed. Lastly, a planar chiral DMAP catalyst is introduced. In Chapter 2, the preparation of a novel camphor-derived bipyridine ligand precursor is described. The discussion includes the careful design of the ligand structure based on several considerations and a 10-step synthesis starting from camphor. In Chapter 3, the stereoselective functionalization of the ligand precursor and the synthesis of bipyridine ligands are discussed. Two chiral 2,2’-bipyridine ligands are prepared as a proof of concept of the tunability. In Chapter 4, we discuss ongoing work towards the development of a planar chiral DMAP catalyst that avoids the chiral resolution during the preparation. The synthesis of the catalyst precursor is described. | |
| dcterms.extent | 183 pages | |
| dcterms.language | en | |
| dcterms.publisher | University of Hawai'i at Manoa | |
| dcterms.rights | All UHM dissertations and theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner. | |
| dcterms.type | Text | |
| local.identifier.alturi | http://dissertations.umi.com/hawii:11964 |
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