Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines

被引：81
作者：
Cai, Zhong-Jian [1 ]
Wang, Shun-Yi [1 ]
Ji, Shun-Jun [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 13期
基金：
中国国家自然科学基金;
关键词：
C(sp(3))H functionalization; copper; dehydrogenative coupling; imidazo[1; 2-a]pyridines; oxygen; ONE-POT SYNTHESIS; MOLECULAR-OXYGEN; ALPHA-KETOAMIDES; BOND FORMATION; CATALYZED OXIDATION; COUPLING REACTIONS; OXIDASE CATALYSIS; FACILE SYNTHESIS; N-HETEROCYCLES; C-C;
D O I：
10.1002/adsc.201300333
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Compared with the well-known palladium-catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2-a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen-mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2-aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp(3))H functionalization.
引用
收藏
页码：2686 / 2692
页数：7
相关论文
共 88 条
[1]   Asymmetric organocatalytic [3+2]-annulation strategy for the synthesis of N-fused heteroaromatic compounds [J].
Albrecht, Lukasz ;
Albrecht, Anna ;
Ransborg, Lars Krogager ;
Jorgensen, Karl Anker .
CHEMICAL SCIENCE, 2011, 2 (07) :1273-1277
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], 2011, ANGEW CHEM
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], 2013, ANGEW CHEM
[6]   BENZIMIDAZOLE CONDENSED RING-SYSTEM .9. POTENTIAL ANTINEOPLASTICS - NEW SYNTHESIS OF SOME PYRIDO[1,2-A]BENZIMIDAZOLES AND RELATED DERIVATIVES [J].
BADAWEY, E ;
KAPPE, T .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (04) :327-332
[7]   Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale [J].
Bagdi, Avik Kumar ;
Rahman, Matiur ;
Santra, Sougata ;
Majee, Adinath ;
Hajra, Alakananda .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1741-1747
[8]   A facile access to 2-methylthio/alkoxy/amino-3-acylimidazo[1,2-a]pyridines based on cupric chloride promoted oxidative ring closure of α-oxoketene N,S-, N,O-, and N,N-acetals [J].
Barun, HO ;
Ila, H ;
Junjappa, H ;
Singh, OM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1583-1587
[9]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[10]  
Brasche G., 2008, ANGEW CHEM, V120, P1958
123456789