Yang Cheng, Arora Sahil, Maldonado Stephen, Pratt Derek A, Stephenson Corey R J
Willard Henry Dow Laboratory, Department of Chemistry, University of Michigan, Ann Arbor, MI, USA.
Program in Applied Physics, University of Michigan, Ann Arbor, MI, USA.
Nat Rev Chem. 2023 Sep;7(9):653-666. doi: 10.1038/s41570-023-00511-z. Epub 2023 Jul 18.
Phthalimide-N-oxyl (PINO) is a valuable hydrogen-atom-transfer (HAT) catalyst for selective C-H functionalization. To advance and optimize PINO-catalysed HAT reactions, researchers have been focused on modifying the phthalimide core structure. Despite much effort and some notable advances, the modifications to date have centred on optimization of a single parameter of the catalyst, such as reactivity, solubility or stability. Unfortunately, the optimization with respect to one parameter is often associated with a worsening of the others. The derivation of a single catalyst structure with optimal performance across multiple parameters has therefore remained elusive. Here we present an analysis of the structure-activity relationships of PINO and its derivatives as HAT catalysts, which we hope will stimulate further development of PINO-catalysed HAT reactions and, ultimately, lead to much improved catalysts for real-world applications.
邻苯二甲酰亚胺 - N - 氧基（PINO）是一种用于选择性C - H官能化的重要氢原子转移（HAT）催化剂。为了推进和优化PINO催化的HAT反应，研究人员一直致力于修饰邻苯二甲酰亚胺核心结构。尽管付出了很多努力并取得了一些显著进展，但迄今为止的修饰都集中在优化催化剂的单个参数上，例如反应性、溶解性或稳定性。不幸的是，针对一个参数的优化往往会导致其他参数变差。因此，尚未找到一种在多个参数上都具有最佳性能的单一催化剂结构。在此，我们对PINO及其衍生物作为HAT催化剂的构效关系进行了分析，希望这将推动PINO催化的HAT反应的进一步发展，并最终为实际应用带来性能大幅提升的催化剂。
