Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes
文献类型：期刊论文
| 作者 | Jiang, Biao-Lin1,2; Xu, Bao-Hua2; Wang, Meng-Liang1; Li, Zeng-Xi3; Liu, Dian-Sheng1; Zhang, Suo-Jiang2 |
| 刊名 | ASIAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2018-05-01 |
| 卷号 | 7期号:5页码:977-983 |
| 关键词 | amidation cobalt esterification radicals oxidation |
| ISSN号 | 2193-5807 |
| DOI | 10.1002/ajoc.201800118 |
| 英文摘要 | A protocol for a Co-II/N,N',N''-trihydroxyisocyanuric acid (THICA)-catalyzed aerobic oxidative esterification and amidation of aldehydes has been developed. Preliminary insight into the mechanism indicates that such an oxidative C-O/N cross-coupling reaction proceeds by masking the aldehyde in a nucleophilic addition reaction with an alkoxy/amino source, thereby keeping the highly reactive formyl group from undesired oxidation. This protocol for the oxidative esterification and amidation of aldehydes proceeds through two different pathways that are characterized by the intrinsic nucleophilicity of the alkanol and amine sub-strates The former occurs in the presence of p-CH3C6H4SO3H as a cocatalyst and orthoformates as the alkoxy sources, instead of alkanols, to efficiently afford the transient acetals. In contrast, the coupling of the more nucleophilic amines with aldehydes renders a readily accessible cross-coupling reaction that occurs without any cocatalyst but is limited by the potential inhibition of THICA upon nucleophilic substitution by an amine. Consequently, only sterically hindered amines were tolerated in this catalytic system, whereas further condensation occurred in the presence of primary amines to lead to imines. |
| WOS关键词 | N-HYDROXYPHTHALIMIDE NHPI ; POLARITY-REVERSAL CATALYST ; HYDROXY PHTHALIMIDE NHPI ; AROMATIC METHYL-ESTERS ; ONE-POT SYNTHESIS ; METAL-FREE ; MILD CONDITIONS ; ALPHA-KETOAMIDES ; BENZYL ALCOHOLS ; AMIDE SYNTHESIS |
| 资助项目 | National Natural Science Foundation of China[21476240] ; Instrument Developing Project of the Chinese Academy of Science[YZ201521] ; Chinese Academy of Science 100-Talent Program ; Key Program of National Natural Science Foundation of China[91434203] ; Key Research Program of Frontier Sciences, CAS[QYZDY-SSW-JSC011] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000435746300021 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 资助机构 | National Natural Science Foundation of China ; Instrument Developing Project of the Chinese Academy of Science ; Chinese Academy of Science 100-Talent Program ; Key Program of National Natural Science Foundation of China ; Key Research Program of Frontier Sciences, CAS |
| 源URL | [http://ir.ipe.ac.cn/handle/122111/25041]  |
| 专题 | 中国科学院过程工程研究所 |
| 通讯作者 | Xu, Bao-Hua; Liu, Dian-Sheng |
| 作者单位 | 1.Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Shanxi, Peoples R China 2.Chinese Acad Sci, State Key Lab Multiphase Complex Syst, Beijing Key Lab Ion Liquids Clean Proc, Key Lab Green Proc & Engn,Inst Proc Engn, Beijing 100190, Peoples R China 3.Grad Univ, Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jiang, Biao-Lin,Xu, Bao-Hua,Wang, Meng-Liang,et al. Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY,2018,7(5):977-983. |
| APA | Jiang, Biao-Lin,Xu, Bao-Hua,Wang, Meng-Liang,Li, Zeng-Xi,Liu, Dian-Sheng,&Zhang, Suo-Jiang.(2018).Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes.ASIAN JOURNAL OF ORGANIC CHEMISTRY,7(5),977-983. |
| MLA | Jiang, Biao-Lin,et al."Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes".ASIAN JOURNAL OF ORGANIC CHEMISTRY 7.5(2018):977-983. |
入库方式： OAI收割
来源：过程工程研究所
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