Nickel-catalyzed C-P cross-coupling of diphenylphosphine oxide with aryl chlorides

被引:91
作者
Zhang, Hong-Yu [1 ]
Sun, Meng [1 ]
Ma, Yan-Na [1 ]
Tian, Qiu-Ping [1 ]
Yang, Shang-Dong [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
LIGANDS; PHOSPHINES; HALIDES;
D O I
10.1039/c2ob26874d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel protocol for the preparation of various diarylphosphine oxide compounds via a Ni-catalyzed cross-coupling of aryl chlorides with R2P(O)H has been developed. Notably, this process exhibits the following very attractive features: (i) the process is simpler and operates under mild reaction conditions; (ii) the process is generally cheaper in part because the more accessible aryl chloride is used to form the C-P bond; (iii) the process avoids the need for simultaneous preparation and use of Ar2P(O)M.
引用
收藏
页码:9627 / 9633
页数:7
相关论文
共 37 条
[1]   Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors [J].
Alexandre, Francois-Rene ;
Amador, Agnes ;
Bot, Stephanie ;
Caillet, Catherine ;
Convard, Thierry ;
Jakubik, Jocelyn ;
Musiu, Chiara ;
Poddesu, Barbara ;
Vargiu, Luana ;
Liuzzi, Michel ;
Roland, Arlene ;
Seifer, Maria ;
Standring, David ;
Storer, Richard ;
Dousson, Cyril B. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :392-395
[2]  
[Anonymous], 2006, WO PCT Int. Appl., Patent No. 054182
[3]   Catalytic synthesis of phosphines and related compounds [J].
Baillie, C ;
Xiao, JL .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (05) :477-514
[4]   Catalytic methods for building up phosphorus-carbon bond [J].
Beletskaya, IP ;
Kazankova, MA .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) :1391-1430
[5]   Inhibitors of protein tyrosine phosphatases: Next-generation drugs? [J].
Bialy, L ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3814-3839
[6]   Bond dissociation energies of organic molecules [J].
Blanksby, SJ ;
Ellison, GB .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263
[7]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
[8]   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
[9]  
Diederich F., 1998, Metal-Catalyzed Cross-Coupling Reactions
[10]  
Engel R., 1988, SYNTHESIS CARBON PHO