Palladium-Catalyzed Oxidative Arylation of Tertiary Benzamides: Para-Selectivity of Monosuhstituted Arenes

被引:42
作者
Yang, Ze [1 ]
Qiu, Fang-Cheng [1 ]
Gao, Juan [1 ]
Li, Zeng-Wen [1 ]
Guan, Bing-Tao [1 ,2 ]
机构
[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, State Key Lab & Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
关键词
C-H ACTIVATION; ARYL BOND FORMATION; COUPLING REACTIONS; FUNCTIONALIZATION; ALKENYLATION; RHODIUM(III); OLEFINATION; C(SP(2))-H; ANILIDES; ALKYNES;
D O I
10.1021/acs.orglett.5b02135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient protocol for the high para-selective arylation of monosubstituted arenes with tertiary benzamides has been developed via palladium-catalyzed oxidative coupling reactions. Due to the mild conditions and the easy availability of substrates and oxidant, this method could potentially provide a practical approach for the synthesis of para-substituted biaryl compounds.
引用
收藏
页码:4316 / 4319
页数:4
相关论文
共 58 条
[21]   Gold-catalyzed direct oxidative coupling reactions of non-activated arenes [J].
Kar, Anirban ;
Mangu, Naveenkumar ;
Kaiser, Hanns Martin ;
Tse, Man Kin .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :524-537
[22]   Synthesis of Phenanthridinones from N-Methoxybenzamides and Arenes by Multiple Palladium-Catalyzed C-H Activation Steps at Room Temperature [J].
Karthikeyan, Jaganathan ;
Cheng, Chien-Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (42) :9880-9883
[23]   Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines [J].
Kim, Junwon ;
Jo, Mina ;
So, Wonyoung ;
No, Zaesung .
TETRAHEDRON LETTERS, 2009, 50 (11) :1229-1235
[24]   Beyond Directing Groups: Transition-Metal-Catalyzed C-H Activation of Simple Arenes [J].
Kuhl, Nadine ;
Hopkinson, Matthew N. ;
Wencel-Delord, Joanna ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10236-10254
[25]   Chelate-Assisted Oxidative Coupling Reaction of Arylamides and Unactivated Alkenes: Mechanistic Evidence for Vinyl C-H Bond Activation Promoted by an Electrophilic Ruthenium Hydride Catalyst [J].
Kwon, Ki-Hyeok ;
Lee, Do W. ;
Yi, Chae S. .
ORGANOMETALLICS, 2010, 29 (22) :5748-5750
[26]   Arylation of unactivated arenes [J].
Lei, Aiwen ;
Liu, Wei ;
Liu, Chao ;
Chen, Mao .
DALTON TRANSACTIONS, 2010, 39 (43) :10352-10361
[27]   Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components [J].
Li, Bi-He ;
Tian, Shi-Liang ;
Fang, Zhao ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1115-1118
[28]   Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation [J].
Li, Bi-Jie ;
Yang, Shang-Dong ;
Shi, Zhang-Jie .
SYNLETT, 2008, (07) :949-957
[29]   From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation [J].
Li, Bi-Jie ;
Shi, Zhang-Jie .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (17) :5588-5598
[30]   Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential C-H and C-N Cleavage [J].
Li, Bi-Jie ;
Wang, Hao-Yuan ;
Zhu, Qi-Lei ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) :3948-3952