Thesis advisor: Shih-Yuan Liu / Described herein are four projects focused on the elaboration of aromatic 1,2-azaborine core structures through late-stage functionalization strategies. In the first chapter, the gram scale, protecting group-free synthesis of the direct BN isostere of benzene is developed. This protocol is used to produce large quantities of pure 1,2-azaborine suitable for use in fundamental investigations. Second, the first general solution for the functionalization of the C4, C5, and C6 ring positions of 1,2-azaborines is described, featuring iridium catalyzed C-H borylation as the key strategy. Azaborine boronates produced via this method are successfully elaborated through cross coupling and oxidation to access azaborines that serve as N,N-ligands for electrophilic boron sources. The third project is an extension of the borylation/cross coupling project, and introduces the first polymer consisting of repeating azaborine units that displays highly efficient extension of conjugation along the azaborine chain. Finally, a copper catalyzed radical process is developed that enables removal of azaborine boron protecting groups during synthetic routes to simple azaborine targets of high interest. / Thesis (PhD) — Boston College, 2016. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_105027 |
| Date | January 2016 |
| Creators | Baggett, Andrew William |
| Publisher | Boston College |
| Source Sets | Boston College |
| Language | English |
| Detected Language | English |
| Type | Text, thesis |
| Format | electronic, application/pdf |
| Rights | Copyright is held by the author. This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-nc-sa/4.0). |
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