2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

被引:532
作者
Pace, Vittorio [1 ,2 ]
Hoyos, Pilar [1 ]
Castoldi, Laura [3 ]
Dominguez de Maria, Pablo [4 ]
Alcantara, Andres R. [1 ]
机构
[1] Univ Complutense, Dept Organ & Pharmaceut Chem, E-28040 Madrid, Spain
[2] Univ Vienna, Dept Drug & Nat Prod Synth, A-1090 Vienna, Austria
[3] Univ Pavia, Dept Pharmaceut Chem, I-27100 Pavia, Italy
[4] Rhein Westfal TH Aachen, ITMC, D-52074 Aachen, Germany
关键词
biocatalysis; green chemistry; organocatalysis; solvent effects; renewable resources; PHOSPHINE-PHOSPHITE LIGANDS; GRIGNARD-REAGENTS; GREEN CHEMISTRY; BIOTRANSFORMATIONS; 1,4-ADDITION; PATHWAYS; CLEAVAGE; LIPASE; ALDOL; THF;
D O I
10.1002/cssc.201100780
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Methyl-tetrahydrofuran (2-MeTHF) can be derived from renewable resources (e.g., furfural or levulinic acid) and is a promising alternative solvent in the search for environmentally benign synthesis strategies. Its physical and chemical properties, such as its low miscibility with water, boiling point, remarkable stability compared to other cyclic-based solvents such as THF, and others make it appealing for applications in syntheses involving organometallics, organocatalysis, and biotransformations or for processing lignocellulosic materials. Interestingly, a significant number of industries have also started to assess 2-MeTHF in several synthetic procedures, often with excellent results and prospects. Likewise, preliminary toxicology assessments suggest that the use of 2-MeTHF might even be extended to more processes in pharmaceutical chemistry. This Minireview describes the properties of 2-MeTHF, the state-of-the-art of its use in synthesis, and covers several outstanding examples of its application from both industry and academia.
引用
收藏
页码:1369 / 1379
页数:11
相关论文
共 92 条
  • [21] Practical approaches to green solvents
    DeSimone, JM
    [J]. SCIENCE, 2002, 297 (5582) : 799 - 803
  • [22] HOMOLOGATION OF L-PHENYLALANINE TO KETOMETHYLENE AND HYDROXYETHYLENE DIPEPTIDE ISOSTERES VIA 2-THIAZOLYL AMINO KETONE INTERMEDIATE
    DONDONI, A
    PERRONE, D
    [J]. TETRAHEDRON LETTERS, 1992, 33 (47) : 7259 - 7262
  • [23] The importance of Green Chemistry in Process Research and Development
    Dunn, Peter J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) : 1452 - 1461
  • [24] Design and Scale-Up of Diels-Alder Reactions for the Practical Synthesis of 5-Phenylbicyclo[2.2.2]oct-5-en-2-one
    Funel, Jacques-Alexis
    Schmidt, Gunther
    Abele, Stefan
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (06) : 1420 - 1427
  • [25] Solvents in organic synthesis:: Replacement and multi-step reaction systems
    Gani, Rafiqul
    Gomez, Paola Arenas
    Folic, Milica
    Jimenez-Gonzalez, Concepcion
    Constable, David J. C.
    [J]. COMPUTERS & CHEMICAL ENGINEERING, 2008, 32 (10) : 2420 - 2444
  • [26] Selective and Flexible Transformation of Biomass-Derived Platform Chemicals by a Multifunctional Catalytic System
    Geilen, Frank M. A.
    Engendahl, Barthel
    Harwardt, Andreas
    Marquardt, Wolfgang
    Klankermayer, Juergen
    Leitner, Walter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) : 5510 - 5514
  • [27] Development of an Efficient Large-Scale Synthesis for a 4H-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide Derivative for Depression and Anxiety
    Giubellina, Nicola
    Stabile, Paolo
    Laval, Gilles
    Perboni, Alcide D.
    Cimarosti, Zadeo
    Westerduin, Pieter
    Cooke, Jason W. B.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (04) : 859 - 867
  • [28] Lipases:: Useful biocatalysts for the preparation of pharmaceuticals
    Gotor-Fernandez, Vicente
    Brieva, Rosario
    Gotor, Vicente
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2006, 40 (3-4) : 111 - 120
  • [29] Process development of the synthetic route to r116301
    Guillaume, Michel
    Cuypers, Jef
    Dingenen, Jul
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (06) : 1079 - 1086
  • [30] Highly alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents
    Hatano, M
    Matsumura, T
    Ishihara, K
    [J]. ORGANIC LETTERS, 2005, 7 (04) : 573 - 576