Recent Developments on Supported Hydrogen-bond Organocatalysts

被引:28
作者
Franconetti, Antonio [1 ]
de Gonzalo, Gonzalo [2 ]
机构
[1] Univ Autonoma Barcelona, Dept Quim, Cerdanyola Del Valles 01893, Spain
[2] Univ Seville, Dept Quim Organ, C Prof Garcia Gonzalez 2, E-41012 Seville, Spain
关键词
heterogeneous catalysis; immobilization; hydrogen-bond catalysts; mesoporous silica; copolymerization; ASYMMETRIC ALPHA-AMINATION; NITRO-MICHAEL ADDITION; IONIC-LIQUID; RECYCLABLE ORGANOCATALYST; 1,3-DICARBONYL COMPOUNDS; MESOPOROUS SILICA; HIGHLY EFFICIENT; BIFUNCTIONAL ORGANOCATALYSTS; THIOUREA ORGANOCATALYSTS; CONTINUOUS-FLOW;
D O I
10.1002/cctc.201801459
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Hydrogen-bond organocatalysts are a family of Bronsted acid organic compounds able to activate electrophilic substrates toward nucleophilic addition through hydrogen bonding interactions. Since the first report using these catalysts, they have been widely exploited in several valuable processes, in general with high activities and selectivities. The immobilization of hydrogen-bond catalysts affords heterogeneous systems which enable different features for a green chemistry approach, such as chemical and mechanical stability, easy work-up and/or reusability. Several kinds of supports have been employed for immobilization while maintaining the advantages of the homogeneous catalysts. In the present review, we have mainly focused our attention in the immobilization of ureas, thioureas and squaramides organocatalysts onto various supports, including polymeric materials, mesoporous silicas, nanoparticles and ionic liquids, and also some copolymerization processes have been described. In addition, the role of these supported organocatalysts published since 2010 on different stereoselective transformations has been evaluated.
引用
收藏
页码:5554 / 5572
页数:19
相关论文
共 139 条
[1]   Novel bifunctional chiral urea and thiourea derivatives as organocatalysts:: Enantioselective nitro-Michael reaction of malonates and diketones [J].
Andres, Jose M. ;
Manzano, Ruben ;
Pedrosa, Rafael .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (17) :5116-5119
[2]   Biodegradable Chitosan-Derived Thioureas as Recoverable Supported Organocatalysts - Application to the Stereoselective Aza-Henry Reaction [J].
Andres, Jose M. ;
Gonzalez, Fernando ;
Maestro, Alicia ;
Pedrosa, Rafael ;
Valle, Maria .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (25) :3658-3665
[3]   Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions [J].
Andres, Jose M. ;
Ceballos, Miriam ;
Maestro, Alicia ;
Sanz, Isabel ;
Pedrosa, Rafael .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 :628-635
[4]   Bottom-Up Synthesis of Supported Thioureas and Their Use in Enantioselective Solvent-Free Aza-Henry and Michael Additions [J].
Andres, Jose M. ;
de La Cruz, Noelia ;
Valle, Maria ;
Pedrosa, Rafael .
CHEMPLUSCHEM, 2016, 81 (01) :86-92
[5]   Polystyrene supported benzoylthiourea-pyrrolidine organocatalyst for the enantioselective Michael addition [J].
Androvic, Ladislav ;
Drabina, Pavel ;
Svobodova, Marketa ;
Sedlak, Milos .
TETRAHEDRON-ASYMMETRY, 2016, 27 (16) :782-787
[6]  
[Anonymous], 2010, Angew. Chem., DOI DOI 10.1002/ANGE.200905684
[7]  
[Anonymous], 2017, ANGEW CHEM
[8]  
[Anonymous], 2010, Angew. Chem, DOI DOI 10.1002/ANGE.200903924
[9]  
[Anonymous], 2006, ANGEW CHEM
[10]   Defining the hydrogen bond: An account (IUPAC Technical Report) [J].
Arunan, Elangannan ;
Desiraju, Gautam R. ;
Klein, Roger A. ;
Sadlej, Joanna ;
Scheiner, Steve ;
Alkorta, Ibon ;
Clary, David C. ;
Crabtree, Robert H. ;
Dannenberg, Joseph J. ;
Hobza, Pavel ;
Kjaergaard, Henrik G. ;
Legon, Anthony C. ;
Mennucci, Benedetta ;
Nesbitt, David J. .
PURE AND APPLIED CHEMISTRY, 2011, 83 (08) :1619-1636