Examination of the Factors Influencing Boron-Mediated Cleavage of Inert C-O Bonds

C-O键的选择性断裂在有机化学领域是一个持续不断的挑战，也是一个非常感兴趣的领域，因为C-O键存在于许多自然生成的化合物和材料中。这种键的选择性切割有望成为从复杂聚合物中生成有用的小分子原料的一种方法。我们在威廉姆斯实验室的合作者最近的工作证明了三卤化硼混合物在调节选择性C-O键断裂方面的潜在能力。拟议的研究合作将结合Williams和Davis研究小组的实验和计算优势，提供第一个关于硼介导的C-O键断裂的反应性和选择性的通用模型。每个小组采用的反应设计技术将首次结合起来，培训学生最先进的反应发展和机械技术，同时也作为原理证明，这些方法结合在一起在提高反应发展速度方面的力量。从这项工作中获得的信息将被用来设计新的可用于分解和回收环氧塑料的硼刘易斯酸。这将通过开发一种可持续和可再生的环氧树脂来源来对抗石油基环氧树脂对环境的负面影响。从这项工作中获得的知识和开发的硼物种将有助于解决日益严重的全球塑料污染问题。

Selective cleavage of C-O bonds is an ongoing challenge in the field of organic chemistry and is an area of great interest as C-O bonds are found in many naturally occurring compounds and materials. The selective cleavage of this linkage holds promise as a way of generating useful small molecule feedstocks from complex polymers. Recent work by our collaborators in the Williams lab has demonstrated the potential power of mixtures of boron trihalides in mediating selective C-O bond cleavage. The proposed research collaboration will combine the experimental and computational strengths of the Williams and Davis research groups to provide the first general model of reactivity and selectivity for boron mediated C-O bond cleavage. The reaction design techniques employed by each group will be combined for the first time to train students in state-of the-art reaction development and mechanistic techniques while also serving as proof of principle for the power of combining these methods in advancing the rate of reaction development. The information gained from this work will then be leveraged to design new boron Lewis acids which can be applied to the breakdown and recycling of epoxy plastics. This will combat the negative environmental impacts of petroleum-based epoxy resins by developing a sustainable and renewable source of epoxy resins. The knowledge gained from this work and the boron species developed will help to address the growing global issue of plastic pollution.