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Synthesis of Pyrrole-2-carbaldehyde Derivatives by Oxidative Annulation and Direct Csp3–H to C═O Oxidation
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-12 00:00:00 , DOI: 10.1021/acs.orglett.7b03821
Xia Wu 1 , Peng Zhao 1 , Xiao Geng 1 , Can Wang 1 , Yan-dong Wu 1 , An-xin Wu 1, 2
Affiliation  

An efficient and practical de novo synthesis of pyrrole-2-carbaldehyde skeletons featuring oxidative annulation and Csp3–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.

中文翻译:

氧化环化和C sp 3–H直接氧化为C═O合成吡咯-2-甲醛衍生物

提出了一种高效且实用的从头合成吡咯-2-甲醛骨架的方法,该骨架具有氧化环化反应和C sp 3–H到C═O氧化反应,以由芳基甲基酮,芳基胺和乙酰乙酸酯。初步的机理研究表明,醛中的氧原子起源于氧。此外,已开发的可扩展方法相对于C–H部分的传统氧化功能化具有明显优势,避免了使用化学计量的危险氧化剂。
更新日期:2018-01-12
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