Suzuki-Miyaura coupling reaction by PdII-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group

被引:289
作者
Shi, Zhangjie [1 ]
Li, Bijie
Wan, Xiaobing
Cheng, Jiang
Fang, Zhao
Cao, Bin
Qin, Changming
Wang, Yang
机构
[1] Chinese Acad Sci, State Keu Lab Organomet Chem, Shanghai 200032, Peoples R China
[2] Peking Univ, PKU Green Chem Ctr, Coll Chem, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
[3] Peking Univ, Coll Med, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[4] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 3250027, Peoples R China
关键词
C-C coupling; C-H activation; electrophilic substitution; palladium; Suzuki-Miyaura reaction;
D O I
10.1002/anie.200700590
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A seamless join: An efficient method to construct a C(sp2)-C(sp2) bond has been developed by using a Suzuki-Miyaura-type coupling of N-alkyl acetanilides with boronic acids. The reaction was catalyzed by a PdII species and the C-H bond activation was directed by the acetamino group (see scheme). This reaction offers a halogen-free method to construct complicated structures. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5554 / 5558
页数:5
相关论文
共 86 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]  
[Anonymous], 2002, ANGEW CHE
[3]  
[Anonymous], 2002, J ORGANOMET CHEM
[4]  
Bedford RB, 2002, ANGEW CHEM INT EDIT, V41, P4120, DOI 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO
[5]  
2-7
[6]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[7]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[8]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[9]   1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles [J].
Campo, MA ;
Huang, QH ;
Yao, TL ;
Tian, QP ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11506-11507
[10]   Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].
Cárdenas, DJ ;
Martín-Matute, B ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040