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1.1.4.1.5 Hydroformylation of Alkenes in Fluorous Phases

DOI: 10.1055/sos-SD-212-00096

Mortreux, A.; Sauthier, M.; Monflier, E.; Tilloy, S.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20141176.

As already emphasized, separating the catalyst from products and recycling it is an important issue considering the high price of the metal and ligands. Previous sections in this chapter have described the use of water/organic solvent and ionic liquid/organic biphasic systems, the interest coming from the possibility of recycling the catalysts. Ionic liquids were introduced as they also allow reactions using higher alkenes, and another approach uses perfluorinated solvents. Fluorous solvents afford biphasic mixtures with most organic compounds and thus open the possibility for biphasic catalysis. Horváth and Rábai have shown that fluorous biphasic systems can be highly successful in the post-reaction separation of the catalyst from products.[‌44‌,‌45‌] The critical factor in designing an efficient catalyst for application in fluorous biphasic systems is the high solubility of the catalyst in the perfluorinated solvent.[‌46‌] In a rhodium-catalyzed hydroformylation system, the solubility is conferred to the catalyst by the addition of perfluoroalkyl chains to the phosphorus ligands,[‌47‌‌50‌] e.g. in phosphite 31 (Scheme 14), which can be synthesized according to reported procedures.[‌51‌,‌52‌]

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