The overarching objective of this research plan is to develop a greater understanding of the unique chemistry of boron trihalides and exploit this chemistry in developing new chemical transformations. Specifically, we intend to:
- Develop a greater understanding of stoichiometric balance between boron trihalides and reactants; in other words, can boron trihalides deliver all three halides groups?
- Exploit the Lewis acidity of boron trihalides to synthesize various bicyclic ring structures.
- Synthesize various dialkyl triazenes and study the boron trihalide-facilitated degradation of these functional groups as a new route leading to aryl halides.
Significance in Achieving the Research Goals
Goal 1. Develop a greater understanding of stoichiometric ratio between boron trihalides and reactants. Achieving this goal is of fundamental importance because of the little is known about the reaction pathways for numerous boron trihalides-facilitated reactions. For instance, it wasn’t until our group in 2015 confirmed the mechanistic pathways for boron-tribromide mediated ether cleavage that was originally developed in 1942. In addition, controlling the stoichiometric balance between Lewis acids and substrates minimizes side reactions and undesired products.
Goal 2. Exploit the Lewis acidity of boron trihalides to synthesize various bicyclic ring structures. Using boron trihalides as a Lewis acid for bicyclic ring formations address two important fundamental questions. First, by developing novel synthetic methodology that uses boron trihaleds as a Lewis acid leads to unique boron-containing ring structures that can be derivatize through palladium cross-coupling (i.e. Suzuki cross-coupling). Secondly, we believe that the materials themselves may have interesting and useful properties in areas of anti-microbial and anti-fungal agents.
Goal 3. Synthesize various dialkyl triazenes and study the boron trihalide-facilitated degredation of these functional groups as a new route leading to aryl halides. We hypothesize that dialkyl triazenes, which are commonly used as masking groups for cross-coupling, may be degraded using boron trihalides under mild reactions conditions and smoothly lead to arylhalides. Futhermore, we hypothesize that selective decomposition of the dialkyl triazene moiety can be controlled be the first example of orthogonal“deprotection” of this functional group.
Over the past five years, my undergraduate research team has made significant contributions to the field of boron trihalides. We have published two papers in this area and have two papers in preparations. We describe an ambitions five-year research plan that will expand prior knowledge of classic organic transformations as well as develop new boron trihalide-mediated reactions. In short our goal is to synergistically blend undergraduate education and leading edge research.