Polymer supported DMAP: an easily recyclable organocatalyst for highly atom-economical Henry reaction under solvent-free conditions

被引:22
作者
Das, Diparjun [1 ]
Pathak, Gunindra [1 ]
Rokhum, Lalthazuala [1 ]
机构
[1] Natl Inst Technol Silchar, Dept Chem, Silchar 788010, Assam, India
来源
RSC ADVANCES | 2016年 / 6卷 / 106期
关键词
SOLID-PHASE SYNTHESIS; NITROALDOL-REACTION; GREEN CHEMISTRY; AQUEOUS-MEDIA; CATALYST; EFFICIENT; ACYLATION; ALCOHOLS; BASE; HYDROTALCITE;
D O I
10.1039/c6ra23696k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polymer supported catalysts are regarded as a borderline class of catalysts, which retains the advantages of homogeneous catalysts while securing the ease of recovery by simple filtration and workup of heterogeneous systems. Additionally, such catalysts are less hygroscopic due to the long polymer backbone. Here we have demonstrated that a catalytic amount of polymer supported DMAP (10 mol%) can lead to excellent conversion of an equimolar mixture of aldehyde and nitroalkane exclusively into beta-nitroalcohols via the Henry reaction. Unlike most of the commonly used catalysts, polymer supported DMAP can be recovered by simple filtration and reused several times, thereby reducing the operational cost. High synthetic efficiency, total atom economy, near quantitative yields, mild reaction conditions, operational simplicity, easy recovery and reusability of the catalyst, solvent-free reaction conditions and avoidance of traditional reaction workup make the protocol highly significant from Green and Sustainable Chemistry perspectives.
引用
收藏
页码:104154 / 104163
页数:10
相关论文
共 62 条
  • [51] Heterogeneous Organocatalysis at Work: Functionalization of Hollow Periodic Mesoporous Organosilica Spheres with MacMillan Catalyst
    Shi, Jiao Yi
    Wang, Chang An
    Li, Zhi Jun
    Wang, Qiong
    Zhang, Yuan
    Wang, Wei
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) : 6206 - 6213
  • [52] Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts for nonenzymatic enantioselective acylations
    Spivey, AC
    Fekner, T
    Spey, SE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3154 - 3159
  • [53] Synthesis and applications of small molecule libraries
    Thompson, LA
    Ellman, JA
    [J]. CHEMICAL REVIEWS, 1996, 96 (01) : 555 - 600
  • [54] Chiral tetraaminophosphonium salt-mediated asymmetric direct henry reaction
    Uraguchi, Daisuke
    Sakaki, Sawako
    Ooi, Takashi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12392 - +
  • [55] Wade PA, 1990, NITRO COMPOUNDS RECE, P137
  • [56] A green chemistry approach to asymmetric catalysis: Solvent-free and highly concentrated reactions
    Walsh, Patrick J.
    Li, Hongmei
    Anaya de Parrodi, Cecilia
    [J]. CHEMICAL REVIEWS, 2007, 107 (06) : 2503 - 2545
  • [57] Dual-reagent organocatalysis with a phosphine and electron-deficient alkene: application to the Henry reaction
    Wang, Xiu
    Fang, Fan
    Zhao, Chen
    Tian, Shi-Kai
    [J]. TETRAHEDRON LETTERS, 2008, 49 (45) : 6442 - 6444
  • [58] Polymeric Graphitic Carbon Nitride as a Heterogeneous Organocatalyst: From Photochemistry to Multipurpose Catalysis to Sustainable Chemistry
    Wang, Yong
    Wang, Xinchen
    Antonietti, Markus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) : 68 - 89
  • [59] Phosphonium Salt Organocatalysis
    Werner, Thomas
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (10) : 1469 - 1481
  • [60] Chiral dialkylaminopyridine catalysts in asymmetric synthesis
    Wurz, Ryan P.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5570 - 5595