Glucose as a Clean and Renewable Reductant in the Pd-Nanoparticle-Catalyzed Reductive Homocoupling of Bromo- and Chloroarenes in Water

被引:75
作者
Monopoli, Antonio [1 ]
Calo, Vincenzo
Ciminale, Francesco
Cotugno, Pietro
Angelici, Carlo
Cioffi, Nicola
Nacci, Angelo [1 ]
机构
[1] Univ Aldo Moro, Dept Chem, CNR ICCOM, I-70126 Bari, Italy
关键词
CROSS-COUPLING REACTIONS; ARYL HALIDES; HETEROGENEOUS CATALYST; ALKALINE-DEGRADATION; IONIC LIQUIDS; PALLADIUM; SUZUKI; CARBON; BIARYLS; COMPOSITES;
D O I
10.1021/jo1005729
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly sustainable Ullmann-type homocoupling of bromo- and chloroarenes, including the more challenging electron-rich chloroarenes (e.g., 4-chloroanisole). catalyzed by in situ generated Pd colloids, is carried Out in aqueous medium under relatively mild conditions (temperatures ranging from 40 to 90 degrees C). Glucose is used as a clean and renewable reductant. while tetra butylammonium hydroxide (TBAOH) acts as base, surfactant, and phase-transfer agent, creating a favorable environment for the catalyst. Pd nanoparticle sizes, morphology, and chemical composition are ascertained by TEM and XPS analyses.
引用
收藏
页码:3908 / 3911
页数:4
相关论文
共 43 条
[1]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].
Alonso, Francisco ;
Beletskaya, Irina P. ;
Yus, Miguel .
TETRAHEDRON, 2008, 64 (14) :3047-3101
[2]  
[Anonymous], 1995, Handbook of X-ray Photoelectron Spectroscopy. A Reference Book of Standard Spectra for Identification and Interpretation of XPS Data
[3]  
Baudoin O., 2003, Studies in Natural Product Chemistry, V29, P355, DOI DOI 10.1016/S1572-5995(03)80011-X
[4]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[5]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[6]   Modified BINAP: The how and the why [J].
Berthod, M ;
Mignani, G ;
Woodward, G ;
Lemaire, M .
CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836
[7]  
Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1
[8]   BINOL: A versatile chiral reagent [J].
Brunel, JM .
CHEMICAL REVIEWS, 2005, 105 (03) :857-897
[9]   Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].
Calò, V ;
Nacci, A ;
Monopoli, A ;
Montingelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :6040-6044
[10]   Effects of ionic liquids on Pd-catalysed carbon-carbon bond formation [J].
Calo, Vincenzo ;
Nacci, Angelo ;
Monopoli, Antonio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (17) :3791-3802