Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines

被引:82
作者
Zhang, Hong-Yu [1 ]
Mao, Liu-Liang [1 ]
Yang, Bin [1 ]
Yang, Shang-Dong [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
关键词
MONOSUBSTITUTED PHOSPHINIC ACIDS; ALKENE CARBOAMINATION REACTIONS; P BOND CONSTRUCTION; C-H BONDS; UNACTIVATED ALKENES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HETEROCYCLE SYNTHESIS; CONJUGATED DIENES; PALLADIUM;
D O I
10.1039/c4cc10267c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product.
引用
收藏
页码:4101 / 4104
页数:4
相关论文
共 110 条
[71]   Development of Intramolecular Vicinal Diamination of Alkenes: From Palladium to Bromine Catalysis [J].
Muniz, Kilian ;
Martinez, Claudio .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2168-2174
[72]   High-Oxidation-State Palladium Catalysis: New Reactivity for Organic Synthesis [J].
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9412-9423
[73]   Platinum-catalysed aerobic 1,2-aminooxygenation of alkenes [J].
Muniz, Kilian ;
Iglesias, Alvaro ;
Fang, Yewen .
CHEMICAL COMMUNICATIONS, 2009, (37) :5591-5593
[74]   Transition-metal-catalyzed reactions in heterocyclic synthesis [J].
Nakamura, I ;
Yamamoto, Y .
CHEMICAL REVIEWS, 2004, 104 (05) :2127-2198
[75]   A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine [J].
Nicolai, Stefano ;
Piemontesi, Cyril ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (20) :4680-4683
[76]   Mechanistic Analysis and Optimization of the Copper-Catalyzed Enantioselective Intramolecular Alkene Aminooxygenation [J].
Paderes, Monissa C. ;
Keister, Jerome B. ;
Chemler, Sherry R. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02) :506-515
[77]   Evidence for Alkene cis-Aminocupration, an Aminooxygenation Case Study: Kinetics, EPR Spectroscopy, and DFT Calculations [J].
Paderes, Monissa C. ;
Belding, Lee ;
Fanovic, Branden ;
Dudding, Travis ;
Keister, Jerome B. ;
Chemler, Sherry R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (06) :1711-1726
[78]   Manganese(III)-mediated phosphinoyl radical reactions for stereoselective synthesis of phosphinoylated tetrahydronaphthalenes [J].
Pan, Xiang-Qiang ;
Wang, Lu ;
Zou, Jian-Ping ;
Zhang, Wei .
CHEMICAL COMMUNICATIONS, 2011, 47 (27) :7875-7877
[79]   Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development [J].
Sambiagio, Carlo ;
Marsden, Stephen P. ;
Blacker, A. John ;
McGowan, Patrick C. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3525-3550
[80]   Stereoselective Synthesis of Morpholines via Copper-Promoted Oxyamination of Alkenes [J].
Sequeira, Fatima C. ;
Chemler, Sherry R. .
ORGANIC LETTERS, 2012, 14 (17) :4482-4485