Catalyst-Free Decarboxylation of Carboxylic Acids and Deoxygenation of Alcohols by Electro-Induced Radical Formation

被引：61

作者：

Chen, Xiaoping ^{[1
]}

Luo, Xiaosheng ^{[2
]}

Peng, Xiao ^{[1
]}

Guo, Jiaojiao ^{[2
]}

Zai, Jiantao ^{[2
]}

Wang, Ping ^{[2
]}

机构：

[1] Shenzhen Univ, Key Lab Optoelect Devices & Syst, Minist Educ & Guangdong Prov, Coll Phys & Optoelect Engn, Shenzhen 518060, Peoples R China

[2] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 15期

基金：

上海市自然科学基金; 中国博士后科学基金; 中国国家自然科学基金;

关键词：

cathodic reduction; decarboxylation; deoxygenation; electrochemistry; radical reaction; LIGHT PHOTOREDOX CATALYSIS; REDOX-ACTIVE ESTERS; VISIBLE-LIGHT; QUATERNARY CARBONS; OXALATES; CONSTRUCTION; ALKYLATION; COUPLINGS; OXIDATION;

D O I：

10.1002/chem.201905224

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electro-induced reduction of redox active esters and N-phthalimidoyl oxalates derived from naturally abundant carboxylic acids and alcohols provides a sustainable and inexpensive approach to radical formation via undivided electrochemical cells. The resulting radicals are trapped by an electron-poor olefin or hydrogen atom source to furnish the Giese reaction or reductive decarboxylation products, respectively. A broad range of carboxylic acid (1 degrees, 2 degrees, and 3 degrees) and alcohol (2 degrees and 3 degrees) derivatives are applicable in this catalyst-free reaction, which tolerated a diverse range of functional groups. This method features simple operation, is a sustainable platform, and has broad application.

引用

页码：3226 / 3230

页数：5

共 69 条

[61] Electrochemically Enabled Carbohydroxylation of Alkenes with H2O and Organotrifluoroborates [J].