| Heterogeneous biomimetic aerobic synthesis of 3-iodoimidazo[1,2-a]pyridines via CuOx/OMS-2-catalyzed tandem cyclization/iodination and their late-stage functionalization | |
| Department | ERC国家工程研究中心 |
Meng X(孟旭) ; Yu CY(于超英); Chen GX(陈革新); Zhao PQ(赵培庆); Zhao PQ(赵培庆)
| |
| The second department | osso国家重点实验室 |
| 2015 | |
| Source Publication | Catalysis Scence & Technology
 |
| ISSN | 2044-4753 |
| Volume | 5Pages:372-379 |
| Abstract | In the presence of copper supported on manganese oxide-based octahedral molecular sieves OMS-2 (CuOx/OMS-2), the heterogeneously catalytic, aerobic synthesis of 3-iodoimidazo[1,2-a]pyridines from acetophenones, 2-aminopyridines and I2 via tandem cyclization/iodination in a one-pot manner is achieved. As a heterogeneous catalyst, OMS-2 acts not only as a support for catalytic Cu species but also as an electron-transfer mediator (ETM), which combines with Cu to generate a low-energy pathway for rapid electron transfer. In this way, the biomimetic, catalytic oxidation could directly employ air as a green terminal oxidant under mild conditions, and provide corresponding products with broad substrates in moderate to excellent yields using very low catalyst loading (0.2 mol% Cu). In this process, I2 not only plays the role of catalyst for the initial cyclization, with assistance from CuOx/OMS-2, but also acts as a reactant for the next electrophilic oxidative iodination, which makes the reaction highly atom economic. Besides, the late-stage functionalization of the I-substituted imidazo[1,2-a]pyridines is also demonstrated by various coupling reactions, which show its potential applications in synthetic and pharmaceutical chemistry. Moreover, the catalyst is truly heterogeneous and reusable. |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1039/c4cy00919c |
| Indexed By | SCI |
| If | 5.287 |
| Language | 英语 |
| Funding Project | 催化新工艺研究组 |
| compositor | 第一作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/7012 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） 精细石油化工中间体国家工程研究中心（ERC） |
| Corresponding Author | Zhao PQ(赵培庆) |
| Recommended Citation GB/T 7714 | Meng X,Yu CY,Chen GX,et al. Heterogeneous biomimetic aerobic synthesis of 3-iodoimidazo[1,2-a]pyridines via CuOx/OMS-2-catalyzed tandem cyclization/iodination and their late-stage functionalization[J]. Catalysis Scence & Technology,2015,5:372-379. |
| APA | Meng X,Yu CY,Chen GX,Zhao PQ,&赵培庆.(2015).Heterogeneous biomimetic aerobic synthesis of 3-iodoimidazo[1,2-a]pyridines via CuOx/OMS-2-catalyzed tandem cyclization/iodination and their late-stage functionalization.Catalysis Scence & Technology,5,372-379. |
| MLA | Meng X,et al."Heterogeneous biomimetic aerobic synthesis of 3-iodoimidazo[1,2-a]pyridines via CuOx/OMS-2-catalyzed tandem cyclization/iodination and their late-stage functionalization".Catalysis Scence & Technology 5(2015):372-379. |
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| Catalysis Science & （2491KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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