NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes | |
Department | OSSO国家重点实验室 |
Miao CX(苗成霞)1![]() ![]() ![]() | |
2016 | |
Source Publication | Catalysis Science & Technology
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ISSN | 2044-4753 |
Volume | 6Issue:5Pages:1378-1383 |
Abstract | A mild and selective system comprising N-hydroxyphthalimide (NHPI) and Fe(NO3)3·9H2O was developed for the oxidation of benzylic methylenes with an atmospheric pressure of molecular oxygen at 25 °C. The influences of reaction conditions such as solvent, different metal catalysts and catalyst loading were studied, as well as the kinetics of the oxidation reaction. Various benzylic methylene substrates could be oxidized to the corresponding carbonyl compounds in satisfactory yields with this catalytic system. Hammett analysis suggested that the substrates with electron-donating groups would have higher oxidation rates. Isotopic (18O) labeling experiments provided evidence of the participation of the nitrate anion in the catalytic cycle. In addition, a possible radical mechanism involving hydrogen atom abstraction by PINO (phthalimide-N-oxyl) and nitrate participation for the oxidation of benzylic methylenes in the Fe(NO3)3·9H2O/NHPI/O2 system was proposed. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1039/c5cy01245g |
Funding Organization | the National Natural Science Foundation of China (21103207;21133011);the Western Light Program of Chinese Academy of Sciences (2012);the Youth Innovation Promotion Association, CAS |
Indexed By | SCI |
If | 5.773 |
Language | 英语 |
Funding Project | 生物与仿生催化课题组;均相催化课题组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/19471 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Miao CX(苗成霞); Sun W(孙伟) |
Affiliation | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China |
Recommended Citation GB/T 7714 | Miao CX,Zhao HQ,Zhao QY,et al. NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes[J]. Catalysis Science & Technology,2016,6(5):1378-1383. |
APA | Miao CX.,Zhao HQ.,Zhao QY.,Xia CG.,Sun W.,...&孙伟.(2016).NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes.Catalysis Science & Technology,6(5),1378-1383. |
MLA | Miao CX,et al."NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes".Catalysis Science & Technology 6.5(2016):1378-1383. |
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c5cy01245g.pdf(276KB) | 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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