The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides | |
Department | OSSO国家重点实验室 |
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) | |
2015 | |
Source Publication | Organic Chemistry Frontiers |
ISSN | 2052-4129 |
Volume | 2Issue:10Pages:1313-1317 |
Abstract | 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. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1039/c5qo00204d |
Funding Organization | the Chinese Academy of Sciences;the National Natural Science Foundation of China (21133011;21373246) |
Indexed By | SCI |
If | 4.693 |
Language | 英语 |
Funding Project | 均相催化课题组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/18898 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Li FW(李福伟) |
Affiliation | 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 |
Recommended Citation 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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