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

A novel water soluble phosphine, N,N-dipolyoxyethylene-substituted-4-(diphe nylphosphino) benzenesulfonamide (PEO-DPPSA), is synthesized by ethoxylatio n of 4-(diphenylphosphino) benzenesulfonamide Ph2P-C6H4SO2NH2 (DPPSA) obtai ned from palladium-catalyzed P-C coupling reaction between 4-I-C6H4SO2NH2 a nd Ph2PH. The PEO-DPPSA possesses the same property of inverse temperature- dependent solubility in water (cloud point, C-p) as nonionic surfactants. I nvestigation on the behavior of RhCl3. 3H(2)O/PEO-DPPSA complex in the aque ous-organic biphasic hydroformylation of 1-decene showed that the complex e xhibited 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. (C) 2001 Else vier Science B.V. All rights reserved.