Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation

被引：287

作者：

Lewis, Jared C.

Bergman, Robert G. ^{[1
]}

Ellman, Jonathan A.

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 17期

关键词：

D O I：

10.1021/ja070388z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work.

引用

收藏

页码：5332 / +

页数：3

相关论文

共 28 条

[1] Iridium(III)-induced isomerization of 2-substituted pyridines to N-heterocyclic carbenes [J].

Alvarez, Eleuterio ;

Conejero, Salvador ;

Paneque, Margarita ;

Petronilho, Ana ;

Poveda, Manuel L. ;

Serrano, Oracio ;

Carmona, Ernesto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13060-13061

[2] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[3] 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

[4] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring [J].

Chatani, N ;

Fukuyama, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :493-494

[5] Regioselective functionalization of unreactive carbon-hydrogen bonds [J].

Daugulis, Olafs ;

Zaitsev, Vladimir G. ;

Shabashov, Dmitry ;

Pham, Quynh-Nhu ;

Lazareva, Anna .

SYNLETT, 2006, (20) :3382-3388

[6]

Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

[7]

2-6

[8] Stabilization of NH tautomers of quinolines by osmium and ruthenium [J].

Esteruelas, Miguel A. ;

Fernandez-Alvarez, Francisco J. ;

Onate, Enrique .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13044-13045

[9] Organometallic homogeneous catalysis - Quo vadis? [J].

Herrmann, WA ;

Cornils, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (10) :1048-1067

[10] Catalytic functionalization of arenes and alkanes via C-H bond activation [J].

Jia, CG ;

Kitamura, T ;

Fujiwara, Y .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :633-639