Aromatic C-H coupling with hindered arylboronic acids by Pd/Fe dual catalysts

被引:124
作者
Yamaguchi, Kazuya [1 ]
Kondo, Hiroki [1 ]
Yamaguchi, Junichiro [1 ]
Itami, Kenichiro [1 ,2 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
SUZUKI-MIYAURA REACTION; OXIDATIVE HECK REACTION; ARYL BORONIC ACIDS; DIRECT ARYLATION; BOND ACTIVATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; PALLADIUM CATALYSIS; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE;
D O I
10.1039/c3sc51206a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An aerobic oxidative coupling of arenes/alkenes with arylboronic acids (C-H/C-B coupling) using catalytic Pd(II)-sulfoxide-oxazoline (sox) ligand and iron-phthalocyanine (FePc) has been developed. This dual catalyst system enables the synthesis of sterically hindered heterobiaryls and styrene derivatives under air without stoichiometric co-oxidants. Additionally, this chemistry demonstrated an advance toward an enantioselective biaryl coupling through C-H functionalization.
引用
收藏
页码:3753 / 3757
页数:5
相关论文
共 74 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   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
[3]   Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].
Albicker, Martin R. ;
Cramer, Nicolai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142
[4]   Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].
Anas, Saithalavi ;
Cordi, Alex ;
Kagan, Henri B. .
CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485
[5]   The first ligand-modulated oxidative Heck vinylation. Efficient catalysis with molecular oxygen as palladium(0) oxidant [J].
Andappan, MMS ;
Nilsson, P ;
Larhed, M .
CHEMICAL COMMUNICATIONS, 2004, (02) :218-219
[6]   Aerobic Oxidative Coupling of Arenes and Olefins through a Biomimetic Approach [J].
Babu, Beneesh P. ;
Meng, Xu ;
Backvall, Jan-E. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (13) :4140-4145
[7]  
BACKVALL JE, 1990, J AM CHEM SOC, V112, P5160
[8]   Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].
Ban, Ikuya ;
Sudo, Tomoko ;
Taniguchi, Tadashi ;
Itami, Kenichiro .
ORGANIC LETTERS, 2008, 10 (16) :3607-3609
[9]   C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling [J].
Bermejo, Antonio ;
Ros, Abel ;
Fernandez, Rosario ;
Lassaletta, Jose M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) :15798-+
[10]   Rhodium-Catalyzed C-H Bond Arylation of Arenes [J].
Bouffard, Jean ;
Itami, Kenichiro .
C-H ACTIVATION, 2010, 292 :231-280