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Facile Synthesis of a Monosulfonated Triphenylphosphane (TPPMS) Derived Ligand having Strong π‐Acceptor Character
Author(s) -
Gulyás Henrik,
Bacsik Zoltán,
Szöllősy Áron,
Bakos József
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606003
Subject(s) - chemistry , ligand (biochemistry) , solubility , yield (engineering) , acceptor , ring (chemistry) , selectivity , ionic bonding , trifluoromethyl , catalysis , sodium , phenyl group , medicinal chemistry , organic chemistry , combinatorial chemistry , alkyl , ion , biochemistry , materials science , receptor , physics , metallurgy , condensed matter physics , halogen
Two phenyl rings of triphenylphosphane have been modified by electron‐withdrawing trifluoromethyl groups. A methoxy group has been introduced at the para ‐position of the third ring. Due to the activating effect of the methoxy group, the phosphane can be monosulfonated under mild conditions and with complete selectivity. The novel ligand, sodium 5‐[bis‐(4‐trifluoromethylphenyl)phosphanyl]‐2‐methoxybenzenesulfonate, has been obtained in quantitative yield, and it has an outstanding π‐acceptor capacity among the known sulfonated triarylphosphanes. It is not soluble in water but soluble in light alcohols and ionic liquids. Its solubility properties allow facile catalyst separation without water.