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

被引:39
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
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
[1]  
[Anonymous], 2008, ANGEW CHEM INT ED, DOI DOI 10.1002/ANGE.200801385
[2]   Metal-Catalyzed One-Step Synthesis: Towards Direct Alternatives to Multistep Heterocycle and Amino Acid Derivative Formation [J].
Arndtsen, Bruce A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (02) :302-313
[3]   Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles [J].
Arthuis, Martin ;
Pontikis, Renee ;
Florent, Jean-Claude .
ORGANIC LETTERS, 2009, 11 (20) :4608-4611
[4]   Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction [J].
Awuah, Emelia ;
Capretta, Alfredo .
ORGANIC LETTERS, 2009, 11 (15) :3210-3213
[5]   Palladium pincer complex-catalyzed condensation of sulfonimines and isocyanoacetate to imidazoline derivatives. Dependence of the stereoselectivity on the ligand effects [J].
Aydin, Juhanes ;
Kumar, K. Senthil ;
Eriksson, Lars ;
Szabo, Kalman J. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2585-2594
[6]   Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].
Barnard, Christopher F. J. .
ORGANOMETALLICS, 2008, 27 (21) :5402-5422
[7]  
Beller M, 2000, ANGEW CHEM INT EDIT, V39, P1010, DOI 10.1002/(SICI)1521-3773(20000317)39:6<1010::AID-ANIE1010>3.0.CO
[8]  
2-P
[9]  
Beller M., 2000, ANGEW CHEM, V112, P1026
[10]   Copper(I)-catalyzed diastereoselective formation of oxazolines and N-sulfonyl-2-imidazolines [J].
Benito-Garagorri, David ;
Bocokic, Vladica ;
Kirchner, Karl .
TETRAHEDRON LETTERS, 2006, 47 (49) :8641-8644