Cyclopentadiene-based Bronsted acid as a new generation of organocatalyst for transfer hydrogenation of 2-substituted quinoline derivatives

被引：23

作者：

Qiao, Xiang ^{[1
]}

El-Shahat, Mahmoud ^{[1
,2
]}

Ullah, Bakhtar ^{[1
]}

Bao, Zongbi ^{[1
]}

Xing, Huabin ^{[1
]}

Xiao, Li ^{[3
]}

Ren, Qilong ^{[1
]}

Zhang, Zhiguo ^{[1
]}

机构：

[1] Zhejiang Univ, Coll Chem & Biol Engn, Key Lab Biomass Chem Engn, Minist Educ, Zheda Rd 38, Hangzhou 310027, Zhejiang, Peoples R China

[2] Natl Res Ctr, Chem Ind Res Div, Photochem Dept, 33 EL Bohouth St, Giza 12622, Egypt

[3] Huzhou Univ, Coll Life Sci, Xueshi Rd 1, Huzhou 313000, Peoples R China

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 21期

基金：

中国国家自然科学基金;

关键词：

Cyclopentadiene-based Bronsted acid; Hantzsch ester; Organocatalysis; Quinoline derivatives; Transfer hydrogenation; IRIDIUM-CATALYZED HYDROGENATION; HANTZSCH ESTERS; ASYMMETRIC HYDROGENATION; HETEROAROMATIC-COMPOUNDS; RECENT PROGRESS; CHEMISTRY; DONORS;

D O I：

10.1016/j.tetlet.2017.04.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and readily available cyclopentadiene-based Bronsted acid was employed to catalyze the transfer hydrogenation of 2-substituted quinolines using Hantzsch ester as the hydrogen source. This conceptually new designed organocatalyst demonstrates remarkably high efficiency for this transformation and a variety of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields under mild reaction conditions. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2050 / 2053

页数：4

共 44 条

[1] Stronger bronsted acids
Akiyama, Takahiko
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
[2] Stronger Bronsted Acids: Recent Progress
Akiyama, Takahiko
Mori, Keiji
[J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9277 - 9306
[3] Enantioselective Synthesis of Alcohols and Amines by Iridium-Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes
Bartoszewicz, Agnieszka
Ahlsten, Nanna
Martin-Matute, Belen
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (23) : 7274 - 7302
[4] PENTAKIS(METHOXYCARBONYL)CYCLOPENTADIENE CHEMISTRY .1. PREPARATION AND PROPERTIES OF THE DIENE, AND OF DERIVATIVES CONTAINING THE ALKALI-METALS OR THALLIUM(I) - CRYSTAL AND MOLECULAR-STRUCTURES OF HC5(CO2ME)5, LI[C5(CO2ME)5].H2O, K[C5(CO2ME)5].MEOH, AND TL[C5CO2ME)5]
BRUCE, MI
WALTON, JK
WILLIAMS, ML
HALL, SR
SKELTON, BW
WHITE, AH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (11): : 2209 - 2220
[5] A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles
Chakraborty, Sumit
Brennessel, William W.
Jones, William D.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) : 8564 - 8567
[6] Selective Catalytic Hydrogenation of Heteroarenes with N-Graphene-Modified Cobalt Nanoparticles (Co3O4 Co/NGr@α-Al2O3)
Chen, Feng
Surkus, Annette-Enrica
He, Lin
Pohl, Marga-Martina
Radnik, Jorg
Topf, Christoph
Junge, Kathrin
Beller, Matthias
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) : 11718 - 11724
[7] Chenault H K, 1988, Biotechnol Genet Eng Rev, V6, P221
[8] Asymmetric organocatalytic reductions mediated by dihydropyridines
Connon, Stephen J.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (21) : 3407 - 3417
[9] Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild Conditions by an Outer-Sphere Pathway
Dobereiner, Graham E.
Nova, Ainara
Schley, Nathan D.
Hazari, Nilay
Miller, Scott J.
Eisenstein, Odile
Crabtree, Robert H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) : 7547 - 7562
[10] Small-molecule H-bond donors in asymmetric catalysis
Doyle, Abigail G.
Jacobsen, Eric N.
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5713 - 5743

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