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

被引:56
|
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
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
收藏
页码:3226 / 3230
页数:5
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