Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles

被引:43
作者
Huang, Siqi [1 ]
Li, Huan [1 ]
Sun, Xiangying [2 ]
Xu, Linhua [1 ]
Wang, Lianhui [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Sch Biomed Sci, Engn Res Ctr Mol Med,Minist Educ, Key Lab Fujian Mol Med,Key Lab Xiamen Marine & Ge, Xiamen 361021, Fujian, Peoples R China
[2] Huaqiao Univ, Sch Mat Sci, Xiamen 361021, Fujian, Peoples R China
关键词
N BOND FORMATION; RHODIUM(III)-CATALYZED SYNTHESIS; CATALYZED DIRECT; 4+2 ANNULATION; O BOND; ACTIVATION; ALKYNES; ACCESS; ANTHRANILS; FACILE;
D O I
10.1021/acs.orglett.9b01902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and practical method to construct benzimidazoles via Rh(III)-catalyzed sequential C-H amination and annulation cascade reaction has been developed. The cascade reaction displays high step, atom, and redox economy, is compatible with the air, and has good functional group tolerance and high efficiency. The titled products can be easily further converted into imidazo[4,5-c]acridines, which were observed unique fluorescent properties.
引用
收藏
页码:5570 / 5574
页数:5
相关论文
共 70 条
[1]  
[Anonymous], 2018, ANGEW CHEM, V130, P16787
[2]  
[Anonymous], ANGEW CHEM
[3]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[4]   RhIII-Catalyzed Straightforward Synthesis of Benzophenanthroline and Benzophenanthrolinone Derivatives using Anthranils [J].
Biswas, Aniruddha ;
Sarkar, Souradip ;
Samanta, Rajarshi .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (12) :3000-3004
[5]   Copper-Catalyzed Direct, Regioselective Arylamination of N-Oxides: Studies To Access Conjugated π-Systems [J].
Biswas, Aniruddha ;
Karmakar, Ujjwal ;
Nandi, Shiny ;
Samanta, Rajarshi .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) :8933-8942
[6]   Innate and Guided C-H Functionalization Logic [J].
Brueckl, Tobias ;
Baxter, Ryan D. ;
Ishihara, Yoshihiro ;
Baran, Phil S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :826-839
[7]   Developments Towards Regioselective Synthesis of 1,2-Disubstituted Benzimidazoles [J].
Carvalho, Luisa C. R. ;
Fernandes, Eduarda ;
Marques, M. Manuel B. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12544-12555
[8]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[9]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[10]   Enantioselective Silver-Catalyzed Cascade Synthesis of Fused Lactone and Lactam Oxazolines [J].
de la Campa, Raquel ;
Manzano, Ruben ;
Calleja, Paul ;
Ellis, Sam R. ;
Dixon, Darren J. .
ORGANIC LETTERS, 2018, 20 (19) :6033-6036