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1.1.4.1.2.1 Hydroformylation of Alkenes in Room-Temperature Classical Ionic Liquids

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, (20141170.

High recyclability of the catalyst cannot be achieved with triphenylphosphine/rhodium-based catalysts, as severe leaching is observed due to their lipophilic properties.[‌21‌] Due to its ionic character, the sulfonated phosphine 1 has been recognized to be much more suitable. Applied to the hydroformylation of hex-1-ene, variation of the counteranion in 3-butyl-1-methyl-1H-imidazol-3-ium salts proved to be particularly useful for improving catalyst efficiency (Scheme 6).[‌22‌] Thus, kinetic comparisons of imidazolium hexafluorophosphate 12, imidazolium tetrafluoroborate 13, and imidazolium 4-toluenesulfonate 14 show turnover frequencies of 54, 1748, and 2070 h−1, respectively.

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