The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides | |
Li P(李盼)1,2; Zhao JJ(赵静静)1; Xia CG(夏春谷)1; Li FW(李福伟)1; Li FW(李福伟) | |
刊名 | Organic Chemistry Frontiers |
2015 | |
卷号 | 2期号:10页码:1313-1317 |
ISSN号 | 2052-4129 |
通讯作者 | 李福伟 |
英文摘要 | Although radical oxidative coupling provides a powerful C–H functionalization tool, the selective coupling of an electrophilic radical with a heterocyclic electron-deficient C2 site is still a seemingly impossible challenge. In this work, an efficient oxidative C2–H azidation of quinoline N-oxides with TMSN3 has been developed, proceeding at room temperature within 10 min. Based on control experiments and detailed EPR studies, the reaction appears to involve a novel carbene-stabilized N–O radical intermediate, which undergoes a single electron transfer to TMSN3 to give the C2-azidation product. Moreover, this procedure could be smoothly scaled up to gram-synthesis and the products could be converted into other functional heterocycles. |
学科主题 | 物理化学与绿色催化 |
收录类别 | SCI |
资助信息 | the Chinese Academy of Sciences;the National Natural Science Foundation of China (21133011;21373246) |
语种 | 英语 |
WOS记录号 | WOS:000364450000002 |
内容类型 | 期刊论文 |
源URL | [http://210.77.64.217/handle/362003/18898] |
专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
通讯作者 | Li FW(李福伟) |
作者单位 | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China |
推荐引用方式 GB/T 7714 | Li P,Zhao JJ,Xia CG,et al. The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides[J]. Organic Chemistry Frontiers,2015,2(10):1313-1317. |
APA | Li P,Zhao JJ,Xia CG,Li FW,&李福伟.(2015).The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides.Organic Chemistry Frontiers,2(10),1313-1317. |
MLA | Li P,et al."The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides".Organic Chemistry Frontiers 2.10(2015):1313-1317. |
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