Palladium-Catalyzed Aryl Iodide Carbonylation as a Route to Imidazoline Synthesis: Design of a Five-Component Coupling Reaction

被引：40
作者：
Bontemps, Sebastien [1 ,2 ]
Quesnel, Jeffrey S. [1 ,2 ]
Worrall, Kraig [1 ,2 ]
Arndtsen, Bruce A. [1 ,2 ]
机构：
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] Univ Toulouse, UPS, INPT, F-31077 Toulouse, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期
基金：
加拿大自然科学与工程研究理事会;
关键词：
carbonylation; cyclizations; heterocycles; multicomponent reactions; palladium; AMINO-ACID DERIVATIVES; AMIDE BOND FORMATION; MULTICOMPONENT SYNTHESIS; CARBON-MONOXIDE; ENANTIOPURE IMIDAZOLINES; ATMOSPHERIC-PRESSURE; N-SULFONYLIMINES; VINYLIC HALIDES; BETA-LACTAMS; 2-IMIDAZOLINES;
D O I：
10.1002/anie.201103885
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Take five: A new method employing aryl halide carbonylation to directly access heterocycles has been described (see scheme). In a single palladium-catalyzed reaction the catalyst mediates two consecutive carbonylation steps, thereby converting five components (aryl iodide, two units imine, and two units CO) into an imidazoline ring. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8948 / 8951
页数：4
相关论文
共 80 条
[11]   A novel general route for the preparation of enantiopure imidazolines [J].
Boland, NA ;
Casey, M ;
Hynes, SJ ;
Matthews, JW ;
Smyth, MP .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3919-3922
[12]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[13]   Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling-Carbonylation-Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids [J].
Cao, Hong ;
McNamee, Laura ;
Alper, Howard .
ORGANIC LETTERS, 2008, 10 (22) :5281-5284
[14]   Palladium-catalyzed three-component cyclization: Synthesis of hydroisoindol-1-ones from 2-bromocyclohex-1-enecarbaldehydes, anilines and carbon monoxide [J].
Cho, Chan Sik ;
Kim, Hyo Bo ;
Lee, Sang Yeon .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (12-13) :1744-1748
[15]   Synthesis of enantiopure imidazolines through a ritter reaction of 2-(1-aminoalkyl)aziridines with nitriles [J].
Concellón, JM ;
Riego, E ;
Suárez, JR ;
García-Granda, S ;
Díaz, MR .
ORGANIC LETTERS, 2004, 6 (24) :4499-4501
[16]   ACYLPALLADATION OF INTERNAL ALKYNES AND PALLADIUM-CATALYZED CARBONYLATION OF (Z)-BETA-IODOENONES AND RELATED DERIVATIVES PRODUCING GAMMA-LACTONES AND GAMMA-LACTAMS [J].
COPERET, C ;
SUGIHARA, T ;
WU, GZ ;
SHIMOYAMA, I ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3422-3431
[17]   Synthetic routes toward 2-substituted 2-imidazolines [J].
Crouch, R. David .
TETRAHEDRON, 2009, 65 (12) :2387-2397
[18]   Multi-component syntheses of heterocycles by transition-metal catalysis [J].
D'Souza, Daniel M. ;
Mueller, Thomas J. J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108
[19]   Cascade Reactions: Catalytic Synthesis of Functionalized 1,3-Dihydroisobenzofuran and Tetrahydrofuran Derivatives by Sequential Nucleophilic Ring Opening-Heterocyclization-Oxidative Carbonylation of Alkynyloxiranes [J].
Della Ca', Nicola ;
Campanini, Fabio ;
Gabriele, Bartolo ;
Salerno, Giuseppe ;
Massera, Chiara ;
Costa, Mirco .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) :2423-2432
[20]  
Dghaym R.D., 2001, Angew. Chem, V113, P3328
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