| Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde | |
| Department | OSSO国家重点实验室 |
| Li MH(李明浩)1; Gu YL(顾彦龙)1,2; Gu YL(顾彦龙) | |
| 2012 | |
| Source Publication | Advanced Synthesis and Catalysis
 |
| ISSN | 1615-4150 |
| Volume | 354Issue:13Pages:2484-2494 |
| Abstract | The selectivity of a three-component electrophilic reaction of an aldehyde with dimedone and another carbon-based nucleophile could be improved by a reversible alkylation procedure, which involves formation, breaking and regeneration of C-C bonds. In the presence of iron(III) chloride and triphenylphosphine, an analogous C-C bond breaking can be observed in the reaction of 2,3,4,9-tetrahydro-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-1H-xanthen-1-one, in which the fragment of dimedone was replaced by a carbon-based nucleophile. Inspired by this observation, some three-component reactions of salicyldehyde and dimedone were successfully developed by using iron(III) chloride and triphenylphosphine (PPh3) as catalyst. PPh3 plays the role of hydrogen bond acceptor, which confers a good flexibility of the substrate by weakening the intramolecular hydrogen bond, allowing thus an easy interaction of the substrate with iron(III) chloride catalyst. |
| Keyword | Aldehydes C?c?C?c aC?ctivation Dimedone Iron Catalysis Reversible Alkylation Three-component Reaction |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1002/adsc.201200299 |
| Funding Organization | the National Natural Science Foundation of China for financial support (21173089);The Program for new Century Excellent Talents in the University of China (NCET-10-0383);the Chutian Scholar Program of the Hubei Provincial Government;the Specialized Research Fund for the Doctoral Program of Higher Education (20090142120081) |
| Indexed By | SCI |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/3812 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Gu YL(顾彦龙) |
| Affiliation | 1.Huazhong Univ Sci & Technol HUST, Hubei Key Lab Mat Chem & Serv Failure, Sch Chem & Chem Engn, Inst Phys Chem & Ind Catalysis, Wuhan 430074, Peoples R China 2.Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
| Recommended Citation GB/T 7714 | Li MH,Gu YL,Gu YL. Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde[J]. Advanced Synthesis and Catalysis,2012,354(13):2484-2494. |
| APA | Li MH,Gu YL,&顾彦龙.(2012).Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde.Advanced Synthesis and Catalysis,354(13),2484-2494. |
| MLA | Li MH,et al."Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde".Advanced Synthesis and Catalysis 354.13(2012):2484-2494. |
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| File Name/Size | DocType | Version | Access | License | ||
| 31.Adv. Synth. Catal（320KB） | 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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