Manganese complex-catalyzed oxidation and oxidative kinetic resolution of secondary alcohols by hydrogen peroxide | |
Department | 苏州研究院 |
Miao CX(苗成霞)1,2; Li, Xiao-Xi1,3; Yong-Min Lee3; Xia CG(夏春谷)1; Wang Y(王永)1; Wonwoo Nam1,3; Sun W(孙伟)1; Sun W(孙伟) | |
The second department | osso国家重点实验室 |
2017 | |
Source Publication | Chemical Science |
ISSN | 2041-6520 |
Volume | 8Issue:11Pages:7476-7482 |
Abstract | The highly efficient catalytic oxidation and oxidative kinetic resolution (OKR) of secondary alcohols has been achieved using a synthetic manganese catalyst with low loading and hydrogen peroxide as an environmentally benign oxidant in the presence of a small amount of sulfuric acid as an additive. The product yields were high (up to 93%) for alcohol oxidation and the enantioselectivity was excellent (>90% ee) for the OKR of secondary alcohols. Mechanistic studies revealed that alcohol oxidation occurs via hydrogen atom (H-atom) abstraction from an α-CH bond of the alcohol substrate and a two-electron process by an electrophilic Mn-oxo species. Density functional theory calculations revealed the difference in reaction energy barriers for H-atom abstraction from the α-CH bonds of R- and S-enantiomers by a chiral high-valent manganese-oxo complex, supporting the experimental result from the OKR of secondary alcohols. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1039/c7sc00891k |
Funding Organization | the National Natural Science Foundation of China (21473226 to W. S.);the Youth Innovation Promotion Association CAS (2015345 to C. M.);the Natural Science Foundation of Jiangsu Province (BK20161261 to C. M.);the NRF of Korea through CRI (NRF- 2012R1A3A2048842 to W. N.);GRL (NRF-2010-00353 to W. N.) |
Indexed By | SCI |
If | 8.668 |
Language | 英语 |
Funding Project | 仿生与生物催化研究组;均相催化研究组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/22527 |
Collection | 苏州研究院 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Wonwoo Nam; Sun W(孙伟) |
Affiliation | 1.Chinese Acad Sci, LICP, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China 2.Shandong Agr Univ, Coll Chem & Mat Sci, Tai An 271018, Shandong, Peoples R China 3.Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 03760, South Korea |
Recommended Citation GB/T 7714 | Miao CX,Li, Xiao-Xi,Yong-Min Lee,et al. Manganese complex-catalyzed oxidation and oxidative kinetic resolution of secondary alcohols by hydrogen peroxide[J]. Chemical Science,2017,8(11):7476-7482. |
APA | Miao CX.,Li, Xiao-Xi.,Yong-Min Lee.,Xia CG.,Wang Y.,...&孙伟.(2017).Manganese complex-catalyzed oxidation and oxidative kinetic resolution of secondary alcohols by hydrogen peroxide.Chemical Science,8(11),7476-7482. |
MLA | Miao CX,et al."Manganese complex-catalyzed oxidation and oxidative kinetic resolution of secondary alcohols by hydrogen peroxide".Chemical Science 8.11(2017):7476-7482. |
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c7sc00891k.pdf(587KB) | 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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