Ring-opening/1,3-difunctionalization of Cyclopropanes Enabled by Copper Catalysis and Electrochemistry

在化学系化学合成(SYN)项目的支持下，杜克大学的邱旺正在研究环丙烷的化学，以探索它们在有机合成中的潜力。该项目将开发新的催化方法，将容易获得的环丙烷转化为高附加值、功能丰富的有价值的产品，作为在工业和学术界广泛使用的分子构件。拟议的研究还将为从事该研究的研究生提供合成方法学、催化和有机合成方面的强有力的培训。教育活动旨在提高科学、技术、工程和数学(STEM)培训渠道的多样性，扩大学生参与研究的范围，并促进当地社区的推广活动。简单的环丙烷的合成应用于提供多功能的产品，而不需要特定的活化取代基，具有很高的吸引力，但也是尚未解决的挑战。这项应用旨在开发新的活化策略和新方法来实现未活化的环丙烷的选择性开环/1，3-双官能化反应。为了实现这一目标，王博士和她的团队将研究铜催化、电解和光催化，以促进环丙烷的选择性C-C裂解，以实现快速获得在有机合成、药物化学和农用化学中非常受欢迎的各种1，3-双官能化基序和杂环骨架。从长远来看，从这个项目中获得的见解可能会促进与铜催化、电催化、自由基化学和杂环化学相关的新的多组分反应的发明和发展。这一奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Qiu Wang of Duke University is studying the chemistry of cyclopropanes to explore their potential in organic synthesis. This project will develop new catalytic methods that can transform readily available cyclopropanes into high value-added, richly functionalized products of value as molecular building blocks for broad use in industry and academia. The proposed research will also provide engaged graduate students with strong training in synthetic methodology, catalysis, and organic synthesis. The educational activities aim to improve the diversity of the science, technology, engineering, and mathematics (STEM) training pipeline, to broaden student participation in research, and to foster outreach activities for local community.Synthetic applications of simple cyclopropanes to deliver versatile functionalized products without the necessity for specific activating substituents are highly attractive, yet represent unmet challenges. This application aims to develop new activation strategies and novel methods to achieve selective ring-opening/1,3-difunctionalization reactions of non-activated cyclopropanes. To achieve this goal, Dr. Wang and her team will investigate copper-catalysis, electrolysis, and photocatalysis to promote selective C–C cleavage of cyclopropanes to achieve rapid access to diverse 1,3-difunctionalized motifs and heterocyclic frameworks that are highly sought-after in organic synthesis, medicinal chemistry, and agrochemistry. In the longer term, insights obtained from this project will likely facilitate the invention and development of new multi-component reactions related to copper catalysis, electrocatalysis, radical chemistry, and heterocyclic chemistry.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.