Thermoregulated phase transfer ligands and catalysis XIV: Synthesis of N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA) and the catalytic activity of its rhodium complex in hydroformylation of 1-decene

Add time:09/01/2019    Source:sciencedirect.com

A novel water soluble phosphine, N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA), is synthesized by ethoxylation of 4-(diphenylphosphino) benzenesulfonamide Ph2P–C6H4SO2NH2 (DPPSA) obtained from palladium-catalyzed P–C coupling reaction between 4-I–C6H4SO2NH2 and Ph2PH. The PEO-DPPSA possesses the same property of inverse temperature-dependent solubility in water (cloud point, Cp) as nonionic surfactants. Investigation on the behavior of RhCl3·3H2O/PEO-DPPSA complex in the aqueous–organic biphasic hydroformylation of 1-decene showed that the complex exhibited high catalytic activity. The conversion of 1-decene and the yield of aldehydes reach as high as 97.8 and 95.6%, respectively, under optimized conditions. The high reactivity of Rh/PEO-DPPSA complex can be attributed to a process termed thermoregulated phase transfer catalysis.

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