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，杜克大学的王秋（Qiu Wang）正在研究环丙烷的化学性质，以探索其在有机合成中的潜力。该项目将开发新的催化方法，将现成的环丙烷转化为高附加值、高功能化的产品，作为广泛应用于工业和学术界的分子基石。拟议的研究还将为从事合成方法，催化和有机合成的研究生提供强有力的培训。这些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，扩大学生对研究的参与，并促进为当地社区开展外展活动。简单环丙烷的合成应用，以提供多功能功能化产品，而不需要特定的激活取代基是非常有吸引力的，但代表了未满足的挑战。本应用旨在开发新的激活策略和新方法来实现非活化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，从而快速获得各种1,3-二功能化基元和杂环框架，这些基元和杂环框架在有机合成、药物化学和农业化学中非常受欢迎。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。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值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.