N-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N-chlorosuccinimide
文献类型：期刊论文
| 作者 | Li, Zi-Hao1,6; Fiser, Bela2,3; Jiang, Biao-Lin4; Li, Jian-Wei1; Xu, Bao-Hua4,5; Zhang, Suo-Jiang4,5 |
| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2019-04-07 |
| 卷号 | 17期号:13页码:3403-3408 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/c9ob00216b |
| 英文摘要 | The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp(3))-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H. |
| WOS关键词 | AEROBIC OXIDATION ; MOLECULAR-OXYGEN ; AROMATIC-COMPOUNDS ; METAL ; ACID ; HALOGENATION ; EFFICIENT ; ALKANES ; COPPER ; CHLORIDE |
| 资助项目 | National Natural Science Foundation of China[21476240] ; National Natural Science Foundation of China[U1662133] ; EU, Hungary ; European Regional Development Fund[GINOP-2.3.4-15-2016-00004] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000462795100015 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 资助机构 | National Natural Science Foundation of China ; EU, Hungary ; European Regional Development Fund |
| 源URL | [http://ir.ipe.ac.cn/handle/122111/28247]  |
| 专题 | 中国科学院过程工程研究所 |
| 通讯作者 | Li, Jian-Wei; Xu, Bao-Hua |
| 作者单位 | 1.Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China 2.Ferenc Rakoczi II Transcarpathian Hungarian Inst, UA-90200 Beregszasz, Transcarpathia, Ukraine 3.Univ Miskolc, Inst Chem, Computat Mol Design Res Grp, H-3515 Miskolc, Hungary 4.Chinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, Key Lab Green Proc & Engn, State Key Lab Multiphase Complex Syst,Inst Proc E, Beijing 100190, Peoples R China 5.Univ Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China 6.Inst Proc Engn, Beijing, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Zi-Hao,Fiser, Bela,Jiang, Biao-Lin,et al. N-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N-chlorosuccinimide[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2019,17(13):3403-3408. |
| APA | Li, Zi-Hao,Fiser, Bela,Jiang, Biao-Lin,Li, Jian-Wei,Xu, Bao-Hua,&Zhang, Suo-Jiang.(2019).N-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N-chlorosuccinimide.ORGANIC & BIOMOLECULAR CHEMISTRY,17(13),3403-3408. |
| MLA | Li, Zi-Hao,et al."N-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N-chlorosuccinimide".ORGANIC & BIOMOLECULAR CHEMISTRY 17.13(2019):3403-3408. |
入库方式： OAI收割
来源：过程工程研究所
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