Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation

被引:644
作者
García-Cuadrado, D [1 ]
Braga, AAC [1 ]
Maseras, F [1 ]
Echavarren, AM [1 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
关键词
D O I
10.1021/ja056165v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Under the usual conditions, the Pd-catalyzed arylation does not involve an electrophilic aromatic substitution reaction. On the basis of DFT calculations, we propose a mechanism for the Pd-catalyzed arylation that involves a proton abstraction by a carbonate or related ligand and that provides a satisfactory explanation for the experimental data. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1066 / 1067
页数:2
相关论文
共 36 条
[1]   Polyene cyclization by a double intramolecular Heck reaction. A DFT study [J].
Balcells, D ;
Maseras, F ;
Keay, BA ;
Ziegler, T .
ORGANOMETALLICS, 2004, 23 (11) :2784-2796
[2]   C-H bond activation of benzene and methane by M(η2-O2CH)2 (M = Pd or Pt).: A theoretical study [J].
Biswas, B ;
Sugimoto, M ;
Sakaki, S .
ORGANOMETALLICS, 2000, 19 (19) :3895-3908
[3]   Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction [J].
Braga, AAC ;
Morgon, NH ;
Ujaque, G ;
Maseras, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9298-9307
[4]   Novel concepts in directed biaryl synthesis, part 102. The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the 'lactone methodology' [J].
Bringmann, G ;
Tasler, S ;
Pfeifer, RM ;
Breuning, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) :49-65
[5]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[6]   Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis [J].
Campo, MA ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14326-14327
[7]   New catalytic methods for the synthesis of selectively substituted aromatics through palladacycles [J].
Catellani, M ;
Motti, E ;
Faccini, F ;
Ferraccioli, R .
PURE AND APPLIED CHEMISTRY, 2005, 77 (07) :1243-1248
[8]   PALLADACYCLE FORMATION BY ELECTROPHILIC AROMATIC-SUBSTITUTION, AS MONITORED BY H-1-NMR SPECTROSCOPY [J].
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 425 (1-2) :151-154
[9]   Computational study of the mechanism of cyclometalation by palladium acetate [J].
Davies, DL ;
Donald, SMA ;
Macgregor, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13754-13755
[10]  
De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions