Copper-Catalyzed Olefinic C(sp2)-H Activation/Carbene Insertion/Ester Hydrolysis/Cyclization with Aryl Diazo Esters for the Synthesis of Multisubstituted Furanones

被引：8

作者：

Wang, Yuzhi ^{[1
]}

Yu, Yadong ^{[2
]}

Yu, Yang ^{[3
]}

Huang, Fei ^{[1
]}

Baell, Jonathan B. ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Pharmaceut Sci, Nanjing 211816, Peoples R China

[2] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China

[3] Nanjing Tech Univ, Sch Environm Sci & Engn, Nanjing 211816, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 15期

基金：

中国国家自然科学基金;

关键词：

Copper-catalyzed; C-H activation; Carbene insertion; Enaminones; 2(5H)-Furanones; C-H BOND; BUTENOLIDE DERIVATIVES; CARBENE INSERTION; CARBON INSERTION; N-OXIDES; CASCADE; ACCESS; REARRANGEMENT; CONSTRUCTION; HETEROCYCLES;

D O I：

10.1002/adsc.202300494

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A copper-catalyzed olefinic C(sp(2))-H activation/carbene insertion/ester hydrolysis/cyclization sequence has been developed for the synthesis of substituted 2(5H)-furanones employing readily available enaminones and aryl diazo esters as substrates. This method features operationally simple and good functional group tolerance. The transformation could be scaled up to gram quantities and the obtained 2(5H)-furanone derivatives could be easily converted to a wide range of useful synthetic building blocks, indicative of the applicability of the synthetic strategy. Isotope labeling experiments demonstrated the ester group of diazo esters was hydrolyzed during the reaction.

引用

页码：2601 / 2606

页数：6

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