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Production of 2,5-Dihydrofurans and Analogous Compounds

Detailed Technology Description

A powerful single component catalyst system that offers a more economically attractive method to produce 2,5-dihydrofuran and tetrahydrofuran commodity chemical.

Others

• Batory, L. A., et al. (2006). Copper Catalyzed Rearrangement of VinylOxiranes. Journal of American Chemical Society, 128, (50), 16054 -16055.DOI: 10.1021/ja067073o
• Rogers, E., et al. (2007). Highly Selective Copper-Catalyzed RingExpansion of Vinyl Thiiranes: Application to Synthesis of Biotin and theHeterocyclic Core of Plavix. Journal of American Chemical Society, 129,(10), 2768-2769. DOI: 10.1021/ja069059h

*Abstract

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Researchers at Cornell have discovered a powerful single component catalyst system which offers a more economically attractive method to produce 2,5-dihydrofuran and tetrahydrofuran commodity chemicals and building blocks, including preparing a 2,5-dihydrofuran from vinyl oxirane, the reduction of the 2,5-dihydrofuran product to a tetrahydrofuran, and the production of vinyl oxiranes for use in the preparation of 2-methyltetrahydrofuran and 3-methyltetrahydrofuran using an inexpensive, stable and readily available catalyst which can be used with or without an accompanying halide.

These catalysts can also be used to produce:

• 2,5-dihydrothiophenes (the new methodology provides a mild new entry into the thiophene framework as illustrated by our synthetic approaches to biotin, varitriol and Plavix); and
• azabicyclic structures such as 2,5-pyrrolidine and piperidines.

Advantages

• Simple, single component process achieves the same transformations as more complicated multi-component processes - halide is optional
• Activator used is cheap, readily available, and more stable and less toxic than currently used activators
• Simplified purification of product as the only other reagents in the process, used in the first and last steps, are both gases (oxygen and hydrogen)
• Syntheses of 3-MeTHF and 2-MeTHF are very atom economical; unlike most other synthetic approaches, no unnecessary hydroxyl or carbonyl functionalities need to be reduced
• Decreased reaction time
• Process is not limited to the unsubstituted butadiene monoxide substrate and can be applied to a large variety of substituted structures

*Licensing

Jeffrey C. Fearnjcf55@cornell.edu607-254-4502

Country/Region

USA