Henry reaction catalyzed by recyclable polyamine

被引:1
作者
Lv, Bingqing [1 ]
Feng, Qixun [1 ]
Cai, Pengcheng [1 ]
Chen, Guoliang [1 ]
Bao, Xuefei [1 ]
机构
[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
Henry reaction; Polyamine; Catalysis; Nitroaldol addition; 3-dinitroalkanes; ASYMMETRIC HENRY;
D O I
10.1016/j.tetlet.2023.154557
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic Henry reaction is an important CAC bond forming reaction between aldehyde/ketone and nitroalkane. Herein, a metal-free recyclable polyamine JP-2Y was developed and various /3-nitroalcohols were prepared with acceptable yields (up to 91%) via the Henry reaction catalyzed by JP-2Y. In addition, for nitromethane, the protocol can be used for selective preparation of /3-nitro alcohols or 1,3-dinitroalka-nes by adjusting the reaction temperature and additive. The recyclability of JP-2Y was proved via catalyz-ing the reaction at gram-scale for at least 8 consecutive runs.& COPY; 2023 Elsevier Ltd. All rights reserved.
引用
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页数:7
相关论文
共 27 条
[1]   Bis(oxazoline)-Based Coordination Polymers: A Recoverable System for Enantioselective Henry Reactions [J].
Angulo, Beatriz ;
Garcia, Jose I. ;
Herrerias, Clara I. ;
Mayoral, Jose A. ;
Minana, Ana C. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13) :5525-5532
[2]  
Ballini R., 1938, SYNTHESIS, V2004, P2004
[3]   Recent advances in catalysts for the Henry reaction [J].
Bao, Xuefei ;
Li, Xu ;
Jiang, Chunfeng ;
Xiao, Wei ;
Chen, Guoliang .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2022, 75 (10) :806-819
[4]   POLYMER-SUPPORTED SYNTHESIS OF CYCLIC ETHERS - ELECTROPHILIC CYCLIZATION OF TETRAHYDROFUROISOXAZOLINES [J].
BEEBE, X ;
CHIAPPARI, CL ;
OLMSTEAD, MM ;
KURTH, MJ ;
SCHORE, NE .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4204-4212
[5]   Synthesis of (S)-(+)-sotalol and (R)-(-)-isoproterenol via a catalytic enantioselective Henry reaction [J].
Blay, Gonzalo ;
Hernandez-Olmos, Victor ;
Pedro, Jose R. .
TETRAHEDRON-ASYMMETRY, 2010, 21 (05) :578-581
[6]   Catalytic asymmetric Henry reaction [J].
Boruwa, Joshodeep ;
Gogoi, Naminita ;
Saikia, Partha Pratim ;
Barua, Nabin C. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3315-3326
[7]   Nanocrystalline MgO for asymmetric Henry and Michael reactions [J].
Choudary, BM ;
Ranganath, KVS ;
Pal, U ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13167-13171
[8]   Preparation of a Dual-Functionalized Acid-Base Macroporous Polymer via High Internal Phase Emulsion Templating as a Reusable Catalyst for One-Pot Deacetalization-Henry Reaction [J].
Ghanooni, Saeed ;
Karimi, Babak ;
Nikfarjam, Nasser .
ACS OMEGA, 2022, 7 (35) :30989-31002
[9]  
Henry L, 1985, CR HEBD ACAD SCI, V121, P210
[10]   One-Pot High-Yielding Synthesis of the DPP4-Selective Inhibitor ABT-341 by a Four-Component Coupling Mediated by a Diphenylprolinol Silyl Ether [J].
Ishikawa, Hayato ;
Honma, Masakazu ;
Hayashi, Yujiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) :2824-2827