| Silver Migration Facilitates lsocyanide-Alkyne [3+2] Cycloaddition Reactions: Combined Experimental and Theoretical Study | |
| Department | OSSO国家重点实验室 |
Qi, Xiaotian1; Zhang, Heng3; Shao, Ailong2,3; Zhu, Lei1; Xu, Ting1; Gao, Meng2; Liu C(刘超)3,4 ; Lan, Yu1; Liu C(刘超)
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| 2015 | |
| Source Publication | ACS Catalysis
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| ISSN | 2155-5435 |
| Volume | 5Issue:11Pages:6640-6647 |
| Abstract | Silver-mediated isocyanide-alkyne [3 + 2] cycloaddition has been developed as a new method for the synthesis of pyrroles. Density functional theory (DFT) calculations toward this reaction reveal that terminal alkynes participated cycloadditions proceed through two successive 1,5-silver migrations, in which the silver migrates between two carbon atoms and finally returns to original carbon. Natural population analysis (NPA) indicates that silver migration guides the move of charge into a rational way, thereby facilitating the cycloaddition. An analogous silver-migration mechanism is also suitable to explain the reactivity of the cycloaddition between isocyanide and internal alkynes, which shows the generality of the silver-migration process. Moreover, competitive experiments are consistent with the computational results, which provides further support for the mechanism. |
| Keyword | Silver Migration [3+2] Cycloaddition Dft Calculation Npa Charge Competitive Experiments |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1021/acscatal.5b02009 |
| Funding Organization | the National Science Foundation of China (Grants 21372266;51302327;21302148;21272180);the Foundation of 100 Young Chongqing University (Project 0903005203191);the project (No. 106112015CDJZR228806) by the Fundamental Research Funds for Central Universities (Chongqing University) |
| Indexed By | SCI |
| If | 9.307 |
| Language | 英语 |
| compositor | 第四作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/19073 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Gao, Meng; Lan, Yu; Liu C(刘超) |
| Affiliation | 1.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China 2.Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China 3.Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China 4.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst, Lanzhou 730000, Peoples R China |
| Recommended Citation GB/T 7714 | Qi, Xiaotian,Zhang, Heng,Shao, Ailong,et al. Silver Migration Facilitates lsocyanide-Alkyne [3+2] Cycloaddition Reactions: Combined Experimental and Theoretical Study[J]. ACS Catalysis,2015,5(11):6640-6647. |
| APA | Qi, Xiaotian.,Zhang, Heng.,Shao, Ailong.,Zhu, Lei.,Xu, Ting.,...&刘超.(2015).Silver Migration Facilitates lsocyanide-Alkyne [3+2] Cycloaddition Reactions: Combined Experimental and Theoretical Study.ACS Catalysis,5(11),6640-6647. |
| MLA | Qi, Xiaotian,et al."Silver Migration Facilitates lsocyanide-Alkyne [3+2] Cycloaddition Reactions: Combined Experimental and Theoretical Study".ACS Catalysis 5.11(2015):6640-6647. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| acscatal.5b02009.pdf（3262KB） | 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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