Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes

被引:410
作者
Guimond, Nicolas [1 ]
Fagnou, Keith [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
C-H ACTIVATION; POMERANZ-FRITSCH REACTION; INTERNAL ALKYNES; ELECTROPHILIC CYCLIZATION; TERMINAL ACETYLENES; PYRIDINES; IMINES; IMINOANNULATION; DERIVATIVES; CLEAVAGE;
D O I
10.1021/ja904380q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general. rhodium-catalyzed oxidative coupling reaction between internal alkynes and aryl aldimines is described. This process affords 3,4-disubstituted isoquinolines in good yield and high regioselectivity. Preliminary mechanistic studies suggest that the C-N bond formation arises from the reductive elimination of a rhodium(III) species.
引用
收藏
页码:12050 / +
页数:4
相关论文
共 34 条
[1]  
Bischler A., 1893, CHEM BER-RECL, V26, P1903, DOI [10.1002/cber.189302602143, DOI 10.1002/CBER.189302602143]
[2]   POMERANZ-FRITSCH REACTION, ISOQUINOLINE VS OXAZOLES [J].
BROWN, EV .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (19) :3208-3209
[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]   Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3645-3651
[5]   Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of o-(1-alkynyl)benzaldimines [J].
Dai, GX ;
Larock, RC .
ORGANIC LETTERS, 2002, 4 (02) :193-196
[6]   Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-alkynyl)benzaldimines and organic halides [J].
Dai, GX ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :920-928
[7]   Survey of GMP bulk reactions run in a research facility between 1985 and 2002 [J].
Dugger, RW ;
Ragan, JA ;
Ripin, DHB .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (03) :253-258
[8]   Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides [J].
Fischer, Dirk ;
Tomeba, Hisamitsu ;
Pahadi, Nirmal K. ;
Patil, Nitin T. ;
Yamamoto, Yoshinori .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4764-4766
[9]  
Fritsch P., 1893, BER DTSCH CHEM GES, V26, P419
[10]   A Dramatic Substituent Effect in Silver(I) -Catalyzed Regioselective Cyclization of ortho-Alkynylaryl Aldehyde Oxime Derivatives [J].
Gao, Hongyin ;
Zhang, Junliang .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) :85-88