N1-Selective Oxidative C ∼ N Coupling of Azoles with Pyrroles Using a Hypervalent Iodine Reagent

被引：27

作者：

Morimoto, Koji ^{[1
]}

Ohnishi, Yusuke ^{[1
]}

Nakamura, Akira ^{[1
]}

Sakamoto, Kazuma ^{[1
]}

Dohi, Toshifumi ^{[1
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Kusatsu, Shiga 5258577, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 04期

基金：

日本学术振兴会;

关键词：

azoles; indoles; iodine; oxidation; pyrroles; H BOND FUNCTIONALIZATION; CARBONYL-COMPOUNDS; ESTROGEN-RECEPTOR; CROSS-COUPLINGS; CHEMISTRY; INDOLES; REGIOSELECTIVITY; ORGANOCATALYSIS; TRANSANNULATION; CYCLOADDITION;

D O I：

10.1002/ajoc.201400027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for coupling azoles with pyrroles and related compounds using a hypervalent iodine reagent has been developed. The oxidative coupling to produce the CN bond directly from CH and NH bonds is attractive in view of sustainable chemistry by avoiding prefunctionalization of the substrates. Notably, the reactions are found to be N-1-selective at the azoles and tolerant of a broad range of substrates and functional groups.

引用

页码：382 / 386

页数：5

共 50 条

[31] Hypervalent Iodine-Mediated C3-Trifluoropropionyloxylation of N-Substituted Indoles [J].

Tian, Yao ;

Zhou, Ming-Xi ;

Wang, Yue ;

Zeng, Zi-Pei ;

Guo, Yu ;

Zhong, Yuan ;

Zeng, Yao-Fu .

CHEMISTRYSELECT, 2024, 9 (37)

[32] C-N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α-Oxytosylation of Ketones [J].

Alharbi, Haifa ;

Elsherbini, Mohamed ;

Qurban, Jihan ;

Wirth, Thomas .

CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (13) :4317-4321

[33] Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides [J].

Janhsen, Benjamin ;

Studer, Armido .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) :11703-11710

[34] Synthesis of Isoquinoline N-Oxides via Hypervalent Iodine-Mediated Oxidative Cyclization of Ketoximes with Alkenes [J].

Ngamnithiporn, Aurapat ;

Chuentragool, Padon ;

Punnita, Supakarn ;

Thitseesaeng, Wachirawit ;

Sirichai, Teesuda ;

Harada, Shinji ;

Nemoto, Tetsuhiro ;

Ploypradith, Poonsakdi ;

Ruchirawat, Somsak .

JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (24) :8145-8151

[35] Copper-Catalyzed Oxidative C―N Coupling of Carbazoles with Arylglyoxal Hydrates [J].

Zhang, Lianji ;

Pan, Dalong ;

Chu, Jinpeng ;

Zhao, Yuhui ;

Chi, Haijun ;

Dong, Yan ;

Wang, Cuiping ;

Wei, Wanguo ;

Zhang, Zhiqiang .

CHEMISTRYSELECT, 2025, 10 (19)

[36] Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent [J].

Zhang, Xinglu ;

Liu, Zhiqiang ;

Gao, Yu ;

Li, Feng ;

Tian, Yaming ;

Li, Chunju ;

Jia, Xueshun ;

Li, Jian .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) :272-277

[37] N1-Selective alkenylation of 1-sulfonyl-1,2,3-triazoles with alkynes via gold catalysis [J].

Sun, Chenyang ;

Yuan, Xiao ;

Li, Yan ;

Li, Xiaoxiao ;

Zhao, Zhigang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (13) :2721-2724

[38] Domino C-N Coupling/Annulation versus C-N Coupling/Hydroamination of 2-Alkynyl-3-bromobenzothiophenes and 2-Alkynyl-3-bromothiophenes. Highly Efficient Synthesis of Benzothieno[3,2-b]quinolines and Thieno[3,2-b]pyrroles [J].

Salman, Ghazwan Ali ;

Hussain, Munawar ;

Iaroshenko, Viktor ;

Villinger, Alexander ;

Langer, Peter .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :331-336

[39] Direct C-N coupling of azoles with ethers via oxidative C-H activation under metal-organic framework catalysis [J].

Nguyen, Khoa D. ;

Doan, Son H. ;

Ngo, Anh N. V. ;

Nguyen, Tung T. ;

Phan, Nam T. S. .

JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2016, 44 :136-145

[40] Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent [J].

Gieuw, Matthew H. ;

Ke, Zhihai ;

Yeung, Ying-Yeung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (14) :3782-3786

← 1 2 3 4 5 →