297754-74-6Relevant academic research and scientific papers
Water-soluble derivatives of furylphosphanes
Eymery, Frederic,Burattin, Paolo,Mathey, Francois,Savignac, Philippe
, p. 2425 - 2431 (2007/10/03)
(2-Furyl)diphenylphosphane (1), bis(2-furyl)phenylphosphane (8) and tris(2-furyl)phosphane (9) have been converted into their water soluble 5- carboxylates 4, 11 and 12, 5-phosphonates 14 and 16 and 5-sulfinates 17-19. In most cases, the selected route involved a 5-bromo to 5-lithio exchange reaction, followed by reaction with CO2, CIP(O)(OEt)2 or SO2. The furan group sharply enhances the water-solubility of these products when compared with the corresponding benzene derivatives. Catalytic tests in hydrogenation, hydroformylation and Heck cross-coupling reactions showed that the sulfinate group tends to inhibit the catalysis and, in addition, a sharp drop in activity was observed with the trifunctional products 12 and 10. Overall, the phosphonates 14 and 16 appear to be the most promising ligands for biphasic catalysis.
