Bimetallic Nickel Aluminun Mediated Para-Selective Alkenylation of Pyridine: Direct Observation of η2,η1-Pyridine Ni(0)-Al(III) Intermediates Prior to C-H Bond Activation

被引：242

作者：

Tsai, Chung-Chih ^{[1
]}

Shih, Wei-Chih ^{[1
]}

Fang, Cyong-Hui ^{[1
]}

Li, Chia-Yi ^{[1
]}

Ong, Tiow-Gan ^{[1
]}

Yap, Glenn P. A. ^{[2
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei, Taiwan

[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 34期

关键词：

RH(I)-CATALYZED DIRECT ARYLATION; CROSS-COUPLING REACTIONS; AROMATIC HETEROCYCLES; N-OXIDES; FUNCTIONALIZATION; VINYLARENES; ALKYLATION; QUINOLINES; CHLORIDES; CLEAVAGE;

D O I：

10.1021/ja1061246

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have presented new amino-NHC Ni-Al complex mediated para C-H bond activation for pyridine and quinolin, and isolated for the first time the intermediate structure of a bimetallic eta(2),eta(1)-pyridine pyridine nickel aluminum complex prior to its C-H activation, which serves as key evidence for bimetallic catalysis.

引用

收藏

页码：11887 / 11889

页数：3

相关论文

共 32 条

[1] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048

[2] Chelating N-Heterocyclic Carbene Alkoxide as a Supporting Ligand for PdII/IV C-H Bond Functionalization Catalysis [J].

Arnold, Polly L. ;

Sanford, Melanie S. ;

Pearson, Stephen M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (39) :13912-+

[3] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[5] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[6] CuBr-Mediated Oxyalkylation of Vinylarenes under Aerobic Conditions via Cleavage of sp3 C-H Bonds α to Oxygen [J].

Cheng, Kai ;

Huang, Lehao ;

Zhang, Yuhong .

ORGANIC LETTERS, 2009, 11 (13) :2908-2911

[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[8] Energetics of C-H Bond Activation of Fluorinated Aromatic Hydrocarbons Using a [Tp′Rh(CNneopentyl)] Complex [J].

Evans, Meagan E. ;

Burke, Catherine L. ;

Yaibuathes, Sornanong ;

Clot, Eric ;

Eisenstein, Odile ;

Jones, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (37) :13464-13473

[9] Efficient Rh(I)-Catalyzed Direct Arylation and Alkenylation of Arene C-H Bonds via Decarbonylation of Benzoic and Cinnamic Anhydrides [J].

Jin, Weiwei ;

Yu, Zhengkun ;

He, Wei ;

Ye, Wenjing ;

Xiao, Wen-Jing .

ORGANIC LETTERS, 2009, 11 (06) :1317-1320

[10] ISOTOPE EFFECTS IN ARENE C-H BOND ACTIVATION BY [(C5ME5)RH(PME3)] [J].

JONES, WD ;

FEHER, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (16) :4814-4819

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