Design, Synthesis, and Reactivity of Diboryl- and Aminoboryl Carbenes

二硼基卡宾和氨基硼基卡宾的设计、合成和反应性

• 批准号: 2247476
• 负责人: Todd Hudnall
• 金额: $ 50.13万
• 依托单位: Texas State University - San Marcos
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2023
• 资助国家: 美国
• 起止时间: 2023-05-01 至 2026-04-30
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2247476&HistoricalAwards=false
• 关键词: Design; Synthesis; Reactivity; Diboryl; Aminoboryl

is synthesizing compounds of the carbenoid class that formally are electron deficient at carbon. While most compounds feature carbon atoms that form four chemical bonds, there are a handful in which carbons form three or fewer bonds. The isolation of such new carbon species has been impeded by the belief that they are inherently unstable. This project will use methods developed by the PI to prepare compounds called carbenes, which contain only two bonds to carbon. In this project, these methods will be extended to previously unknown carbenes where the carbon atom is bonded to two boron atoms. The availability of these species has the potential to add to our understanding of how chemical reactions of carbon take place, permitting control of the reactivity of carbon-containing compounds. Ultimately, results derived from these studies are expected to advance the manufacturing of fine chemicals and materials by providing more selective approaches to synthesis. Professor Hudnall's laboratory participates in local outreach activities with high schools, a children’s museum to connect the community at large with undergraduate and graduate research.The idea that singlet carbenes feature a p2 electronic configuration has been theorized since the 1960s, but thus far these species have largely eluded isolation in the laboratory. Utilizing synthetic methodologies developed by the principal investigator, diborylcarbenes (R2B-C-BR2) and the related aminoboryl carbenes (R2N-C-BR2) will be prepared. As some of the targeted species may be non-isolable, this research project is seen as a high risk/high reward effort. The targeted diborylcarbenes are predicted to have the p2 electron configuration, a configuration not observed in other carbenes. Importantly, these carbenes are predicted to be quite electrophilic at the carbene carbon atom and may provide opportunities for new manifolds of carbene reactivity.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

是在碳中正式定义的类carbenoid类的合成化合物。虽然大多数化合物具有形成四种化学键的碳原子，但碳形成三个或更少的键。这种新碳物种的隔离受到了这样一种信念，即它们本质上是不稳定的。该项目将使用PI开发的方法来制备称为碳纤维的化合物，该化合物仅包含两种与碳的键。在该项目中，这些方法将扩展到以前未知的碳原子，其中碳原子粘合到两个硼原子。这些物种的可用性有可能增加我们对碳化学反应如何发生的理解，从而可以控制含碳化合物的反应性。最终，这些研究得出的结果有望通过提供更多选择性的合成方法来推动精细化学物质和材料的生产。 Hudnall教授的实验室与高中一起参加了当地的外展活动，这是一个儿童博物馆，旨在将整个社区与本科和研究生研究联系起来。关于单个Carbones具有P2电子配置的想法，自1960年代以来，这些想法已被理论化，但到目前为止，这些物种在实验室中已经很大程度上消失了。利用主要研究者Diborylcarbenes（R2B-C-BR2）开发的合成方法和相关的Aminoboryl Carbones（R2N-C-BR2）。由于某些靶向物种可能没有分离，因此该研究项目被视为高风险/高奖励工作。预计有靶向的Diboryl碳纤维具有P2电子构型，在其他碳纤维中未观察到构型。重要的是，这些碳纤维在卡宾碳原子上被预计是相当亲电的，并且可能为卡宾的新歧管提供机会。反应性。该奖项反映了NSF的法定使命，并通过使用基金会的知识分子优点和更广泛的影响审查标准评估来诚实地表示支持。