Copper-Catalyzed C-P Coupling through Decarboxylation

被引：224
作者：
Hu, Jie [1 ]
Zhao, Ning [1 ]
Yang, Bin [1 ]
Wang, Ge [1 ]
Guo, Li-Na [1 ]
Liang, Yong-Min [1 ]
Yang, Shang-Dong [1 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 20期
关键词：
catalysis; copper; C-P coupling; decarboxylation; phosphorus; HECK-TYPE OLEFINATION; BIARYL SYNTHESIS; ARYL BROMIDES; POTASSIUM POLYFLUOROBENZOATES; AROMATIC CARBOXYLATES; H-PHOSPHONATES; BOND FORMATION; AMINO-ACIDS; PHOSPHORUS; LIGANDS;
D O I：
10.1002/chem.201003561
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An acid for a phosphine: A versatile protocol for preparation of various di(phenyl)phosphoryl oxides was developed by copper-catalyzed decarboxylative coupling of alkenyl, alkynyl carboxylic acids, and N-benzylproline, respectively, with R2P(O)H (see scheme). All classes of products are important precursors for preparation of biologically active molecules and various phosphorus ligands. This finding represents the first example of copper-catalyzed decarboxylative coupling to construct Cï P bonds. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：5516 / 5521
页数：6
相关论文
共 121 条
[21]   Synthesis and Structure of Intermediates in Copper-Catalyzed Alkylation of Diphenylphosphine [J].
Cain, Matthew F. ;
Hughes, Russell P. ;
Glueck, David S. ;
Golen, James A. ;
Moore, Curtis E. ;
Rheingold, Arnold L. .
INORGANIC CHEMISTRY, 2010, 49 (17) :7650-7662
[22]   SYNTHESIS OF SOME NEW PHOSPHINO ACETYLENES [J].
CARTY, AJ ;
HOTA, NK ;
NG, TW ;
PATEL, HA ;
OCONNOR, TJ .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (16) :2706-&
[23]   Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines [J].
Chan, Vincent S. ;
Bergman, Robert G. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15122-+
[24]  
CHARRIER C, 1966, B SOC CHIM FR, P1002
[25]   COPPER-QUINOLINE DECARBOXYLATION [J].
COHEN, T ;
SCHAMBACH, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3189-+
[26]   PRODUCTS AND KINETICS OF DECARBOXYLATION OF ACTIVATED AND UNACTIVATED AROMATIC CUPROUS CARBOXYLATES IN PYRIDINE AND IN QUINOLINE [J].
COHEN, T ;
BERNINGER, RW ;
WOOD, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :837-848
[27]   First synthesis and pharmacological evaluation of benzoindolizidine and benzoquinolizidine analogues of α- and β-peltatin [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Lebrun, S ;
Léonce, S ;
Renard, P ;
Pfeiffer, B .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2113-2125
[28]   ORGANOMETALLIC ACETYLENES OF MAIN GROUPS 3-V [J].
DAVIDSOHN, WE ;
HENRY, MC .
CHEMICAL REVIEWS, 1967, 67 (01) :73-+
[29]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
[30]   Addition of s-h bonds across electron-deficient olefins catalyzed by well-defined copper(I) thiolate complexes [J].
Delp, Samuel A. ;
Munro-Leighton, Colleen ;
Goj, Laurel A. ;
Ramirez, Magaly A. ;
Gunnoe, T. Brent ;
Petersen, Jeffrey L. ;
Boyle, Paul D. .
INORGANIC CHEMISTRY, 2007, 46 (07) :2365-2367
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