Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation

被引:646
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 50 条
[21]   First total synthesis of Dysidavarone A via an intramolecular palladium-catalyzed α-arylation [J].
Schmalzbauer, Bjoern ;
Herrmann, Jennifer ;
Mueller, Rolf ;
Menche, Dirk .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[22]   Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups [J].
Muratake, H ;
Natsume, M ;
Nakai, H .
TETRAHEDRON, 2004, 60 (51) :11783-11803
[23]   Palladium-catalyzed α-arylation of esters [J].
Buchwald, S.L., 1600, American Chemical Society (123)
[24]   Palladium-Catalyzed Arylation of Fluoroalkylamines [J].
Brusoe, Andrew T. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8460-8468
[25]   PALLADIUM-CATALYZED ARYLATION OF DIALKYLPHOSPHITE [J].
NOVIKOVA, ZS ;
DEMIN, NN ;
AGARKOV, AY ;
BELETSKAYA, IP .
ZHURNAL ORGANICHESKOI KHIMII, 1995, 31 (01) :142-142
[26]   Palladium-catalyzed α-arylation of esters [J].
Moradi, WA ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :7996-8002
[27]   Palladium-catalyzed intramolecular carbonyl α-arylation for the synthesis of 2-tetralones [J].
Wang, Lianlian ;
Zhang, Kun ;
Wu, Jie ;
Song, Chuanjun .
TETRAHEDRON LETTERS, 2019, 60 (10) :726-728
[28]   PALLADIUM-CATALYZED ARYLATION OF ETHYLENE [J].
PLEVYAK, JE ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2454-2460
[29]   Palladium-catalyzed arylation of sulfones [J].
Mitin, AV ;
Kashin, AN ;
Beletskaya, IP .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (06) :802-812
[30]   Palladium-catalyzed α-arylation of oxindoles [J].
Durbin, Matthew J. ;
Willis, Michael C. .
ORGANIC LETTERS, 2008, 10 (07) :1413-1415