Premium
Water‐Soluble Derivatives of Furylphosphanes
Author(s) -
Eymery Frédéric,
Burattin Paolo,
Mathey François,
Savignac Philippe
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2425::aid-ejoc2425>3.0.co;2-6
Subject(s) - chemistry , hydroformylation , catalysis , furan , organic chemistry , medicinal chemistry , phosphine , solubility , benzene , rhodium
(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 CO 2 , ClP(O)(OEt) 2 or SO 2 . 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 19 . Overall, the phosphonates 14 and 16 appear to be the most promising ligands for biphasic catalysis.