Sustainable Fluorous Solubilizing Groups

Project: Research

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The fluorous biphasic concept, which led to rapid development of fluorous chemistry, was based on the attachment of perfluoroalkyl-groups to conventional reagents and catalysts in appropriate number and size. The preferred number of carbon atoms of the prefluoroalkyl-groups was in the range of C6-C12 in order to achieve facile and efficient separation. While both, carbon and fluorine are readily available from Nature for even large scale applications, the sustainability of fluorous chemistry has been severely limited by the persistency, toxicity, and long half-lives in humans of compounds containing longer (C6-C12) perfluoroalkyl groups. In particular, the appearance of perfluorooctyl sulfonate and perfluorooctanoic acid (PFOA) in the environment combined with their toxicity have resulted in global concerns and controls. The negative environmental and health impacts of PFOA and related higher homologues have slowed down the development of fluorous chemistry, as any reagents and catalysts containing longer perfluoroalkyl chains could decompose to perfluoroalkyl acids by entering the environment. While limiting the exposure to these compounds could lower the risks, their replacement with alternative shorter perfluoroalkyl groups, which have short half-lives in humans, has been proposed and demonstrated. Therefore, the combination of shorter perfluoroalkyl groups in appropriate numbers at selected positions could provide the necessary fluorous solubility and preferential partition, while upon decomposition they could fall apart to less toxic compounds in the environment. The combination of shorter perfluoroalkyl groups including CF3(CF2)x- (x=0-3), (CF3)3C-, (CF3)3CO-, (CF3)2N-, and (CF3CF2)2N- will be attached to conventional organic reagents, organocatalysts and ligands for transitional catalysts to ensure high solubility and partition to fluorous media. Their evaluation will be done by reactivity, leaching and reusability studies.


Project number7002604
Grant typeSRG
Effective start/end date1/05/101/02/13