Ligand-Promoted C-3 Selective C-H Olefination of Pyridines with Pd Catalysts

被引：294

作者：

Ye, Mengchun ^{[1
]}

Gao, Guo-Lin ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 18期

关键词：

NICKEL/LEWIS ACID CATALYSIS; N-IMINOPYRIDINIUM YLIDES; DIRECT ARYLATION; HETEROAROMATIC-COMPOUNDS; BOND ACTIVATION; AROMATIC HETEROCYCLES; PALLADIUM; ALKENYLATION; BORYLATION; DERIVATIVES;

D O I：

10.1021/ja2021075

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-catalyzed C-3 selective olefination of pyridines is developed for the first time using 1,10-phenanthroline as the ligand. This finding provides a novel disconnection for the synthesis of pyridine-containing alkaloids and drug molecules as well as a new approach for developing Pd-catalyzed C H functionalizations of pyridines.

引用

收藏

页码：6964 / 6967

页数：4

相关论文

共 55 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] Chiral Heterobidentate Pyridine Ligands for Asymmetric Catalysis [J].

Arena, Carmela G. ;

Arico, Girolamo .

CURRENT ORGANIC CHEMISTRY, 2010, 14 (06) :546-580

[4] The bohimann-rahtz pyridine synthesis: From discovery to applications [J].

Bagley, Mark C. ;

Glover, Christian ;

Merritt, Eleanor A. .

SYNLETT, 2007, (16) :2459-2482

[5] Efficient palladium-catalyzed direct arylation of azines and diazines using ligand-free conditions [J].

Baso, Luca ;

Beccalli, Egle M. ;

Borsini, Elena ;

Broggini, Gianluigi .

TETRAHEDRON, 2009, 65 (17) :3486-3491

[6] 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-+

[7] Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover [J].

Campbell, Alison N. ;

White, Paul B. ;

Guzei, Ilia A. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15116-15119

[8] 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

[9] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[10] 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

← 1 2 3 4 5 6 →