Copper-Catalyzed Coupling Reaction of Arylhydrazines and Trialkylphosphites

被引:52
作者
Chen, Sheng-Yan [1 ]
Zeng, Run-Sheng [1 ]
Zou, Jian-Ping [1 ,2 ]
Asekun, Olayinka Taiwo [3 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
[3] Univ Lagos, Dept Chem, Akoka, Yaba, Nigeria
基金
中国国家自然科学基金;
关键词
P BOND CONSTRUCTION; ARYL; LIGAND; VINYL; ARYLATION; HALIDES; ACIDS;
D O I
10.1021/jo4022474
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel CuO-catalyzed coupling reaction of arylhydrazines with trialkyl phosphites to afford arylphosphonates is described. The reaction proceeded at 80 degrees C in air without external reductants, oxidants, and ligands.
引用
收藏
页码:1449 / 1453
页数:5
相关论文
共 27 条
[1]   Microwave-Promoted Palladium(II)-Catalyzed C-P Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates [J].
Andaloussi, Mounir ;
Lindh, Jonas ;
Savmarker, Jonas ;
Sjoberg, Per J. R. ;
Larhed, Mats .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :13069-13074
[2]   Catalytic methods for building up phosphorus-carbon bond [J].
Beletskaya, IP ;
Kazankova, MA .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) :1391-1430
[3]   Arenediazonium tetrafluoroborates in palladium-catalyzed C-P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines [J].
Berrino, Roberta ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Stabile, Paolo .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4518-4520
[4]   Palladium-Catalyzed Cross-Coupling of H-Phosphinate Esters with Chloroarenes [J].
Deal, Eric L. ;
Petit, Christelle ;
Montchamp, Jean-Luc .
ORGANIC LETTERS, 2011, 13 (12) :3270-3273
[5]   P-Arylation: Arynes to Aryl-Phosphonates, -Phosphinates, and -Phosphine Oxides [J].
Dhokale, Ranjeet A. ;
Mhaske, Santosh B. .
ORGANIC LETTERS, 2013, 15 (09) :2218-2221
[6]   Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides [J].
Gelman, D ;
Jiang, L ;
Buchwald, SL .
ORGANIC LETTERS, 2003, 5 (13) :2315-2318
[7]   Recent Advances in Metal-Catalyzed C-P Bond Formation [J].
Glueck, David S. .
C-X BOND FORMATION, 2010, 31 :65-100
[8]  
HIRAO T, 1981, SYNTHESIS-STUTTGART, P56
[9]   Proline/pipecolinic acid-promoted copper-catalyzed P-arylation [J].
Huang, Cheng ;
Tang, Xu ;
Fu, Hua ;
Jiang, Yuyang ;
Zhao, Yufen .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :5020-5022
[10]   A facile route to vinyl- and arylphosphonates by vinyl and aryl radical trapping with (MeO)3P [J].
Jiao, XY ;
Bentrude, WG .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3303-3306