Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles

被引:14
作者
Cui, Xin-Feng [1 ]
Qiao, Xin [1 ]
Wang, He-Song [1 ]
Huang, Guo-Sheng [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Key Lab Nonferrous Met Chem & Resources Utilizat, Dept Chem, Lanzhou 730000, Peoples R China
关键词
Aniline - Polycyclic aromatic hydrocarbons - Scaffolds - Catalysis - Activation analysis - Cyclization - Iridium compounds;
D O I
10.1021/acs.joc.0c01619
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)-anilines and commercially available alpha-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
引用
收藏
页码:13517 / 13528
页数:12
相关论文
共 54 条
[31]   Cp*IrIII-Catalyzed [3+2] Annulations of N-Aryl-2-aminopyrimidines with Sulfoxonium Ylides to Access 2-Alkyl Indoles Through C-H Bond Activation [J].
Luo, Yi ;
Guo, Lingmei ;
Yu, Xinling ;
Ding, Haosheng ;
Wang, Huijing ;
Wu, Yong .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (20) :3203-3207
[32]   Sterically Controlled Ru(II)-Catalyzed Divergent Synthesis of 2-Methylindoles and Indolines through a C - H Allylation/Cyclization Cascade [J].
Manna, Manash Kumar ;
Bairy, Gurupada ;
Jana, Ranjan .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) :8390-8400
[33]  
Marckwald W., 1892, Berichte der Dtsch. Chem. Gesellschaft, V25, P2354, DOI DOI 10.1002/CBER.18920250227
[34]   Palladium on carbon-catalyzed synthesis of 2-and 2,3-substituted indoles under heterogeneous conditions [J].
Monguchi, Yasunari ;
Mori, Shigeki ;
Aoyagi, Satoka ;
Tsutsui, Azusa ;
Maegawa, Tomohiro ;
Sajiki, Hironao .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (14) :3338-3342
[35]   Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates [J].
Ni, Jixiang ;
Jiang, Yong ;
An, Zhenyu ;
Yan, Rulong .
ORGANIC LETTERS, 2018, 20 (06) :1534-1537
[36]   Ruthenium-Catalyzed Regioselective C-H Bond Acetoxylation on Carbazole and Indole Frameworks [J].
Okada, Takeshi ;
Nobushige, Kazunori ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2016, 18 (05) :1150-1153
[37]   Rh(III)-Catalyzed Synthesis of N-Unprotected Indoles from Imidamides and Diazo Ketoesters via C-H Activation and C-C/C-N Bond Cleavage [J].
Qi, Zisong ;
Yu, Songjie ;
Li, Xingwei .
ORGANIC LETTERS, 2016, 18 (04) :700-703
[38]   Hypervalent Iodine(III) Promoted Direct Synthesis of Imidazo[1,2-a]pyrimidines [J].
Qian, Guangyin ;
Liu, Bingxin ;
Tan, Qitao ;
Zhang, Siwen ;
Xu, Bin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (22) :4837-4843
[39]   FISCHER INDOLE SYNTHESIS [J].
ROBINSON, B .
CHEMICAL REVIEWS, 1963, 63 (04) :373-&
[40]   RECENT STUDIES ON FISCHER INDOLE SYNTHESIS [J].
ROBINSON, B .
CHEMICAL REVIEWS, 1969, 69 (02) :227-+