Exploring a unique reactivity of N-heterocyclic carbenes (NHC) in rhodium(III)-catalyzed intermolecular C-H activation/annulation

被引：72

作者：

Ghorai, Debasish ^{[1
]}

Choudhury, Joyanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Organometall & Smart Mat Lab, Bhopal 462066, India

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 96期

关键词：

BOND ACTIVATION; COMPLEXES; ALKYNES; FUNCTIONALIZATION; CATALYSIS; LIGANDS; MOLECULES; INDOLES;

D O I：

10.1039/c4cc07170k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Disclosed herein is the unique conjugative role of N-heterocyclic carbene (NHC) ligands as a directing group in aromatic C-H activation, coupled with a facile NHC-alkenyl annulative reductive elimination which guided the Rh-III-catalyzed intermolecular annulations of imidazolium salts and alkynes under ambient conditions leading to structurally important imidazo[1,2-a]quinolinium motifs.

引用

收藏

页码：15159 / 15162

页数：4

相关论文

共 41 条

[11] Double C-H activation in a Rh-NHC complex leading to the isolation of a 14-electron Rh(III) complex [J].

Dorta, R ;

Stevens, ED ;

Nolan, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5054-5055

[12] The Measure of All Rings-N-Heterocyclic Carbenes [J].

Droege, Thomas ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) :6940-6952

[13] Functionalized N-Heterocyclic Carbene Nonspectator Ligands upon Internal Alkyne Activation Reactions [J].

Fernandez, Francys E. ;

del Carmen Puerta, Maria ;

Valerga, Pedro .

INORGANIC CHEMISTRY, 2013, 52 (11) :6502-6509

[14] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover [J].

Guimond, Nicolas ;

Gouliaras, Christina ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6908-+

[15] Heterocyclic carbenes: Synthesis and coordination chemistry [J].

Hahn, F. Ekkehardt ;

Jahnke, Mareike C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) :3122-3172

[16]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[17]

2-Y

[18] An overview of N-heterocyclic carbenes [J].

Hopkinson, Matthew N. ;

Richter, Christian ;

Schedler, Michael ;

Glorius, Frank .

NATURE, 2014, 510 (7506) :485-496

[19] Novel amidino-substituted thienyl- and furylvinylbenzimidazole:: Derivatives and their photochemical conversion into corresponding diazacyclopenta[c]fluorenes.: Synthesis, interactions with DNA and RNA, and antitumor evaluation.: 4 [J].

Hranjec, Marijana ;

Piantanida, Ivo ;

Kralj, Marijeta ;

Suman, Lidija ;

Pavelic, Kresimir ;

Karminski-Zamola, Grace .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :4899-4910

[20] Rhodium(III)-Catalyzed Direct Selective C(5)-H Oxidative Annulations of 2-Substituted Imidazoles and Alkynes by Double C-H Activation [J].

Huang, Ji-Rong ;

Zhang, Qian-Ru ;

Qu, Chuan-Hua ;

Sun, Xun-Hao ;

Dong, Lin ;

Chen, Ying-Chun .

ORGANIC LETTERS, 2013, 15 (08) :1878-1881

← 1 2 3 4 5 →