Palladium-catalyzed intramolecular Heck dearomative gem-difluorovinylation of indoles

被引：27

作者：

Wang, Gang ^{[1
]}

Li, Wenqi ^{[1
]}

Liu, Tianxiang ^{[1
]}

Zhang, Yonghong ^{[1
]}

Wang, Bin ^{[1
]}

Xue, Fei ^{[1
]}

Jin, Weiwei ^{[1
]}

Ma, Caiyan ^{[1
]}

Xia, Yu ^{[1
]}

Liu, Chenjiang ^{[1
]}

机构：

[1] Xinjiang Univ, Coll Chem,State Key Lab Chem & Utilizat Carbon Ba, Urumqi Key Lab Green Catalysis & Synth Technol, Key Lab Oil & Gas Fine Chem,Minist Educ & Xinjian, Urumqi 830017, Peoples R China

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 39期

基金：

中国国家自然科学基金;

关键词：

DIFLUOROMETHYLATED ARENES; BIOLOGICAL-ACTIVITY; DIAZO-COMPOUNDS; DIFLUOROCARBENE; ACCESS; DIFLUOROOLEFINATION; DIFUNCTIONALIZATION; CONSTRUCTION; OLEFINATION; INDOLINES;

D O I：

10.1039/d2sc03169h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed dearomative reaction of indoles has been developed through a domino Heck/gem-difluorovinylation sequence. By taking advantage of a difluorocarbene precursor (ClCF2COONa), the palladium difluorocarbene ([Pd]=CF2) species was formed smoothly. Then, a migratory insertion/beta-H elimination process enabled access to polycyclic indolines containing 1,1-difluoroethylene units in acceptable yields with a broad substrate scope, which also showed dearomative gem-difluorovinylation for the first time. Remarkably, the superb diversified transformations allowed the product to install various functional groups.

引用

页码：11594 / 11599

页数：6

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