Palladium-Catalyzed Four-Component Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides, Propargyl Amines, and Diaryliodonium Salts: Access to Trifluoromethyl-Containing Trisubstituted Imidazoles

被引:48
作者
Chen, Zhengkai [1 ]
Wang, Wei-Feng [1 ]
Yang, Hefei [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
基金
中国国家自然科学基金;
关键词
EFFICIENT SYNTHESIS; ARYL HALIDES; ISOCYANIDES; FLUORINE; FUNCTIONALIZATION; ALKYNYLATION; CHEMISTRY; IMINES;
D O I
10.1021/acs.orglett.0c00328
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed four-component carbonylative cyclization reaction for the expeditious construction of trifluoromethyl-containing trisubstituted imidazoles has been achieved. With readily accessible trifluoroacetimidoyl chlorides, propargyl amines, and diaryliodonium salts as the starting materials, the carbonylative transformation proceeds smoothly under mild conditions to enable the formation of multifunctionalized imidazole molecules in a one-pot, one-step manner. Diaryliodonium salts serve as both oxidants and aryl sources in the reaction.
引用
收藏
页码:1980 / 1984
页数:5
相关论文
共 55 条
[1]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[2]  
AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737
[3]   Multicomponent Synthesis of Substituted and Fused-Ring lmidazoles via Phospha-munchnone Cycloaddition [J].
Aly, Sara ;
Romashko, Mikhail ;
Arndtsen, Bruce A. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05) :2709-2714
[4]  
Beller M, 2006, TOP ORGANOMETAL CHEM, V18
[5]   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
[6]   Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles [J].
Cai, Jinxiong ;
Bai, Haijie ;
Wang, Yuan ;
Xu, Xianxiu ;
Xie, Haiming ;
Liu, Jun .
CHEMICAL COMMUNICATIONS, 2019, 55 (26) :3821-3824
[7]   Palladium-Catalyzed Ring-Forming Alkene Aminoaroylation of Unsaturated Hydrazones and Sulfonamides [J].
Chen, Jun ;
Yang, Meng-Nan ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
ORGANIC LETTERS, 2018, 20 (11) :3314-3318
[8]   Phosphine-Catalyzed Divergent [4+3] Domino Annulations of CF3-Containing Imines with MBH Carbonates: Construction of Perfluoroalkylated Benzazepines [J].
Chen, Junlong ;
Yin, Zhongmo ;
Huang, You .
ORGANIC LETTERS, 2019, 21 (17) :7060-7064
[9]   Trifluoroacetimidoyl halides: a potent synthetic origin [J].
Chen, Zhengkai ;
Hu, Sipei ;
Wu, Xiao-Feng .
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (02) :223-254
[10]   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