Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides

被引：82
作者：
Crisenza, Giacomo E. M. [1 ]
Sokolova, Olga O. [1 ]
Bower, John F. [1 ]
机构：
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 49期
基金：
英国工程与自然科学研究理事会;
关键词：
acetanilides; branch selectivity; hydroarylation; iridium; phosphine ligands; C-H ACTIVATION; REDUCTIVE ELIMINATION; COUPLING REACTIONS; BOND FORMATION; COMPLEXES; FUNCTIONALIZATION; ARYLATION; INDOLE; ALKENYLATION; STABILITY;
D O I：
10.1002/anie.201506581
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An iridium(I) catalyst system, modified with the wide-bite-angle and electron-deficient bisphosphine d(F)ppb (1,4-bis(di(pentafluorophenyl)phosphino)butane) promotes highly branch-selective hydroarylation reactions between diverse acetanilides and aryl-or alkyl-substituted alkenes. This provides direct and ortho-selective access to synthetically challenging anilines, and addresses long-standing issues associated with related Friedel-Crafts alkylations.
引用
收藏
页码：14866 / 14870
页数：5
相关论文
共 63 条
[1]   Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines [J].
Andou, Takashi ;
Saga, Yutaka ;
Komai, Hirotomo ;
Matsunaga, Shigeki ;
Kanai, Motomu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3213-3216
[2]  
[Anonymous], 2015, ANGEW CHEM
[3]  
[Anonymous], 2013, AM ETHNOL
[4]  
[Anonymous], 2007, Angew. Chem
[5]  
[Anonymous], 2008, ANGEW CHEM
[6]  
[Anonymous], 2015, AM ETHNOL, DOI DOI 10.1002/ANGE.201411518
[7]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[8]   The Selective Cross-Coupling of Secondary Alkyl Zinc Reagents to Five-Membered-Ring Heterocycles Using Pd-PEPPSI-IHeptCl [J].
Atwater, Bruce ;
Chandrasoma, Nalin ;
Mitchell, David ;
Rodriguez, Michael J. ;
Pompeo, Matthew ;
Froese, Robert D. J. ;
Organ, Michael G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) :9502-+
[9]  
Bedford, 2011, ANGEW CHEM, V123, P5638
[10]   Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].
Bedford, Robin B. ;
Haddow, Mairi F. ;
Mitchell, Charlotte J. ;
Webster, Ruth L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527
1234567