Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, P. R. China.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
Org Lett. 2018 Feb 2;20(3):688-691. doi: 10.1021/acs.orglett.7b03821. Epub 2018 Jan 12.
An efficient and practical de novo synthesis of pyrrole-2-carbaldehyde skeletons featuring oxidative annulation and C3-H to C═O oxidation is presented, exemplified by the preparation of pyrrole-2-carbaldehyde derivatives from aryl methyl ketones, arylamines, and acetoacetate esters. Preliminary mechanistic investigations indicate that the aldehyde oxygen atom originates from oxygen. Moreover, the developed scalable approach provides a distinct advantage over traditional oxidative functionalization of C-H moieties, avoiding the use of stoichiometric quantities of hazardous oxidants.
本文提出了一种高效实用的吡咯-2-甲醛骨架的从头合成方法，其特点是氧化环化和 C3-H 到 C═O 氧化，通过芳基甲基酮、芳胺和乙酰乙酸酯的反应制备吡咯-2-甲醛衍生物为例。初步的机理研究表明，醛基中的氧原子来源于氧气。此外，开发的可扩展方法相对于 C-H 部分的传统氧化官能化具有明显的优势，避免了使用大量危险氧化剂。
