Sc(OTf)3-Catalyzed Direct Alkylation of Quinolines and Pyridines with Alkanes

被引：151

作者：

Deng, Guojun ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

SP(3) C-H; PALLADIUM-CATALYZED ALKYLATION; DEHYDROGENATIVE-COUPLING CDC; DIRECT ARYLATION; BOND FORMATION; N-OXIDES; SELECTIVE ALKENYLATION; OXIDATIVE ACTIVATION; AROMATIC-COMPOUNDS; TERTIARY-AMINES;

D O I：

10.1021/ol900070x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Sc(OTf)(3)-catalyzed C-C bond formation by direct alkylation of quinolines and pyridines using simple alkanes was developed. Various alkanes reacted with quinolines and pyridines to give the corresponding alkylation products In 50-91% yields in the presence of tert-butyl peroxide.

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页码：1171 / 1174

页数：4

相关论文

共 67 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].

Ackermann, L ;

Althammer, A ;

Born, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622

[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]

Anastas P., 1998, GREEN CHEM THEORY PR

[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] Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].

Basle, Olivier ;

Li, Chao-Jun .

GREEN CHEMISTRY, 2007, 9 (10) :1047-1050

[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] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[8] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].

Cai, Guixin ;

Fu, Ye ;

Li, Yizhou ;

Wan, Xiaobing ;

Shi, Zhangjie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673

[9] 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

[10]

Campeau LC, 2007, ALDRICHIM ACTA, V40, P35

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