文献类型：期刊文献

英文题名：Direct Cα-heteroarylation of structurally diverse ethers via a mild N-hydroxysuccinimide mediated cross-dehydrogenative coupling reaction

作者：Liu, Shihui[1];Liu, Aoxia[1];Zhang, Yongqiang[1];Wang, Wei[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, State Key Lab Bioengn Reactor, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2017

卷号：8

期号：5

起止页码：4044

外文期刊名：CHEMICAL SCIENCE

收录：;EI(收录号：20172703896690);WOS:【SCI-EXPANDED(收录号:WOS:000400553000089)，CCR-EXPANDED(收录号:WOS:000400553000089)】；

基金：Financial support of this research from the program of National Natural Science Foundation of China (21602060, Y.-Q. Z. and 21372073 and 21572055, W. W.) is gratefully acknowledged.

语种：英文

外文关键词：Free radical reactions - Atoms

摘要：An important challenge in the C alpha-heteroarylation of ethers is the requirement of a large excess amount of ethers (that are used as solvents in many cases) to achieve effective transformations. This drawback has significantly restricted the C alpha-heteroarylation of ethers to the use of simple and easily accessible ether substrates. To overcome this limitation, a new, efficient, N-hydroxysuccinimide (NHS) mediated, mild and metal-free CDC strategy for the direct C alpha-heteroarylation of diverse ethers has been developed. Different to our previous benzaldehyde mediated photoredox C alpha-heteroarylation, we have identified NHS as a new and efficient mediator without using light. A distinct non-photoredox engaged hydrogenatom-transfer (HAT) mechanism that used a nitrogen-centered radical cation produced from NHS is initially revealed. Notably, only 5-10 equivalents of ethers as coupling partners are used, which allows for structurally diverse and complex ethers to engage in this process, to create highly medicinally relevant C alpha-heteroarylated ethers. Furthermore, more structurally diverse heterocyclics can serve as reactants for this process.