Radical α-addition involved electrooxidative [3+2] annulation of phenols and electron-deficient alkenes

被引：22

作者：

Zhao, Qiang ^{[1
]}

Jin, Ji-Kang ^{[1
]}

Wang, Jie ^{[1
]}

Zhang, Feng-Lian ^{[1
]}

Wang, Yi-Feng ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Dept Chem, Ctr Excellence Mol Synth CAS, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 15期

关键词：

ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; N-ACETYL INDOLES; DIHYDROBENZOFURAN LIGNANS; (+)-LITHOSPERMIC ACID; RECENT PROGRESS; CYCLOADDITION; DERIVATIVES; BENZOFUROINDOLINES; (+/-)-SEROTOBENINE; ACCESS;

D O I：

10.1039/d0sc01078b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique alpha-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated.

引用

页码：3909 / 3913

页数：5

共 66 条

[1] Lignans and neolignans as lead compounds [J].