Copper-Catalyzed Radical/Radical C-sp3-H/P-H Cross-Coupling: alpha-Phosphorylation of Aryl Ketone O-Acetyloximes | |
Department | OSSO国家重点实验室 |
Ke J(柯杰)1; Tang, Yuliang1; Yi H(易宏)1; Li, Yali3,4; Cheng, Yongde1; Liu C(刘超)1; Lei AW(雷爱文)1,2; Lei AW(雷爱文) | |
2015 | |
Source Publication | Angewandte Chemie International Edition |
ISSN | 1433-7851 |
Volume | 54Issue:22Pages:6604-6607 |
Abstract | The selective radical/radical cross-coupling of two different organic radicals is a great challenge due to the inherent activity of radicals. In this paper, a copper-catalyzed radical/radical CH/PH cross-coupling has been developed. It provides a radical/radical cross-coupling in a selective manner. This work offers a simple way toward β-ketophosphonates by oxidative coupling of aryl ketone o-acetyloximes with phosphine oxides using CuCl as catalyst and PCy3 as ligand in dioxane under N2 atmosphere at 130 °C for 5 h, and yields ranging from 47 % to 86 %. The preliminary mechanistic studies by electron paramagnetic resonance (EPR) showed that, 1) the reduction of ketone o-acetyloximes generates iminium radicals, which could isomerize to -sp3-carbon radical species; 2) phosphorus radicals were generated from the oxidation of phosphine oxides. Various aryl ketone o-acetyloximes and phosphine oxides were suitable for this transformation. |
Keyword | c(Sp(3))p Bonds Copper Catalysis Oxidative Coupling Radical Radical Cross-coupling -ketophosphonates |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1002/anie.201501287 |
Funding Organization | the 973 Program (2012CB725302;2011CB808600);the National Natural Science Foundation of China (21390400;21272180;21302148);the Research Fund for the Doctoral Program of Higher Education of China (20120141130002);the Program for Changjiang Scholars and Innovative Research Team in University (IRT1030);the Ministry of Science and Technology of China (2012YQ120060);The Program of Introducing Talents of Discipline to Universities of China (111 Program) |
Indexed By | SCI |
If | 11.709 |
Language | 英语 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/18451 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Lei AW(雷爱文) |
Affiliation | 1.Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 3.Nanjing Univ Posts & Telecommun, Key Lab Organ Elect & Informat Display, Nanjing 210023, Jiangsu, Peoples R China 4.Nanjing Univ Posts & Telecommun, Inst Adv Mat, Nanjing 210023, Jiangsu, Peoples R China |
Recommended Citation GB/T 7714 | Ke J,Tang, Yuliang,Yi H,et al. Copper-Catalyzed Radical/Radical C-sp3-H/P-H Cross-Coupling: alpha-Phosphorylation of Aryl Ketone O-Acetyloximes[J]. Angewandte Chemie International Edition,2015,54(22):6604-6607. |
APA | Ke J.,Tang, Yuliang.,Yi H.,Li, Yali.,Cheng, Yongde.,...&雷爱文.(2015).Copper-Catalyzed Radical/Radical C-sp3-H/P-H Cross-Coupling: alpha-Phosphorylation of Aryl Ketone O-Acetyloximes.Angewandte Chemie International Edition,54(22),6604-6607. |
MLA | Ke J,et al."Copper-Catalyzed Radical/Radical C-sp3-H/P-H Cross-Coupling: alpha-Phosphorylation of Aryl Ketone O-Acetyloximes".Angewandte Chemie International Edition 54.22(2015):6604-6607. |
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