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

被引:556
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
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