Mechanistic studies and optimisation of a Pd-catalysed direct arylation reaction using phosphine-free systems

被引:44
作者
Kuwabara, Junpei [1 ]
Sakai, Masaru [1 ]
Zhang, Qiao [1 ]
Kanbara, Takaki [1 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba Res Ctr Interdisciplinary Mat Sci TIMS, Tsukuba, Ibaraki 3058573, Japan
来源
ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 05期
关键词
RECENT PROGRESS; PALLADIUM; COMPLEXES; TRANSMETALATION; ARYLPALLADIUM; HETEROARENES; REDUCTION;
D O I
10.1039/c4qo00351a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The initial step of a Pd-catalysed phosphine-free direct arylation reaction was investigated to provide mechanistic insight, leading to optimisation of the catalytic reaction. On the basis of our observations, the amount of the Pd(OAc)(2) catalyst was reduced to 1 mol%, affording a good yield of the desired product in combination with a reduction in the amount of by-products.
引用
收藏
页码:520 / 525
页数:6
相关论文
共 32 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   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
[3]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[4]   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
[5]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[6]   Microwave-Assisted Polycondensation via Direct Arylation of 3,4-Ethylenedioxythiophene with 9,9-Dioctyl-2,7-dibromofluorene [J].
Choi, Seong Jib ;
Kuwabara, Junpei ;
Kanbara, Takaki .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08) :878-882
[7]   Synthesis of Thiophene- and Bithiophene-Based Alternating Copolymers via Pd-Catalyzed Direct C-H Arylation [J].
Fujinami, Yohei ;
Kuwabara, Junpei ;
Lu, Wei ;
Hayashi, Hideki ;
Kanbara, Takaki .
ACS MACRO LETTERS, 2012, 1 (01) :67-70
[8]  
Hartwig J.F., 2009, Organotransition Metal Chemistry: From Bonding to Catalysis, V1st
[9]  
ITAHARA T, 1984, SYNTHESIS-STUTTGART, P255
[10]   Scope and Limitations of a Direct Arylation Polycondensation Scheme in the Synthesis of PCPDTBT-Type Copolymers [J].
Kowalski, Sebastian ;
Allard, Sybille ;
Scherf, Ullrich .
MACROMOLECULAR RAPID COMMUNICATIONS, 2015, 36 (11) :1061-1068