Solvent-free aryl amination catalysed by [Pd(NHC)] complexes

被引:60
作者
Chartoire, Anthony [1 ]
Boreux, Arnaud [1 ]
Martin, Anthony R. [1 ]
Nolan, Steven P. [1 ]
机构
[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
关键词
N-HETEROCYCLIC CARBENE; CROSS-COUPLING REACTIONS; SUZUKI-MIYAURA; ARYLBORONIC ACIDS; BUCHWALD-HARTWIG; BOND FORMATION; PRE-CATALYST; C-N; EFFICIENT; PRECATALYST;
D O I
10.1039/c3ra40386f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly effective solvent-free protocol for the Buchwald-Hartwig amination of unactivated aryl chlorides is described. The effect of various [Pd(NHC)] pre-catalyst systems on the reactivity has been studied. [Pd(IPr*)(cin)Cl] is reported as the complex of choice for the transformation.
引用
收藏
页码:3840 / 3843
页数:4
相关论文
共 35 条
[1]   Solvent-less and fluoride-free hiyama reaction of arylsiloxanes with aryl bromides and chlorides promoted by sodium hydroxide:: A useful protocol for palladium recycling and product isolation [J].
Alacid, Emilio ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :945-952
[2]   A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction [J].
Bandgar, BP ;
Patil, AV .
TETRAHEDRON LETTERS, 2005, 46 (44) :7627-7630
[3]   Solvent-Free, Microwave-Assisted N-Arylation of Indolines by using Low Palladium Catalyst Loadings [J].
Basolo, Luca ;
Bernasconi, Alice ;
Borsini, Elena ;
Broggini, Gianluigi ;
Beccalli, Egle M. .
CHEMSUSCHEM, 2011, 4 (11) :1637-1642
[4]   IPr* an easily accessible highly hindered N-heterocyclic carbene [J].
Berthon-Gelloz, Guillaume ;
Siegler, Maxime A. ;
Spek, Anthony L. ;
Tinant, Bernard ;
Reek, Joost N. H. ;
Marko, Istvan E. .
DALTON TRANSACTIONS, 2010, 39 (06) :1444-1446
[5]   Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].
Cave, GWV ;
Raston, CL ;
Scott, JL .
CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169
[6]   [Pd(IPr*)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst [J].
Chartoire, Anthony ;
Frogneux, Xavier ;
Boreux, Arnaud ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
ORGANOMETALLICS, 2012, 31 (19) :6947-6951
[7]   An Efficient Palladium-NHC (NHC=N-Heterocyclic Carbene) and Aryl Amination Pre-Catalyst: [Pd(IPr*)(cinnamyl)Cl] [J].
Chartoire, Anthony ;
Frogneux, Xavier ;
Nolan, Steven P. .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1897-1901
[8]   [Pd(IPr*)(cinnamyl)Cl]: An Efficient Pre-catalyst for the Preparation of Tetra-ortho-substituted Biaryls by Suzuki-Miyaura Cross-Coupling [J].
Chartoire, Anthony ;
Lesieur, Mathieu ;
Falivene, Laura ;
Slawin, Alexandra M. Z. ;
Cavallo, Luigi ;
Cazin, Catherine S. J. ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (15) :4517-4521
[9]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
[10]   Bis-Sonogashira cross-coupling: an expeditious approach towards long-chain, phenylene-modified 1,ω-diols [J].
Drescher, Simon ;
Becker, Susan ;
Dobner, Bodo ;
Blume, Alfred .
RSC ADVANCES, 2012, 2 (10) :4052-4054