Synthesis of air-stable zwitterionic 2-phosphiniminium-arenesulfonates

2-[(Dimethylphenylphosphanylidene)azaniumyl]-5-methylbenzenesulfonate benzene monosolvate

“…The structures of the related 2-triphenylphosphiniminium-5-methylbenzenesulfonate and 2-diphenyl(methyl)phosphiniminium-5-methylbenzenesulfonate (Burns et al, 2012), have been reported recently and contain the same primary structural features as those found in (I). All three structures confirm the zwitterionic nature of these compounds via presence of the phosphiniminium group in which the nitrogen is protonated and the sulfonate anion is located ortho to the protonated phosphinimine.…”

“…The smaller phosphiniminium Me 2 PPh substituent in (I) has much less steric impact than the Ph 3 P and Ph 2 PMe groups in the two previously reported zwitterions. Comparison of relevant torsion angles in the three structures shows that the phosphorous atom of the phosphiniminium group in (I) is situated above the plane of the aryl ring of the 5-methylbenzenesulfonate fragment with a C5-C6-N1-P1 torsion angle of 29.7 (2)° whereas the phosphorous atom of the phosphiniminium group in the triphenylphosphiniminium and diphenyl(methyl)phosphiniminium zwitterion structures is located below the plane of the aryl ring with corresponding torsion angles of 39.2 (3)° and 14.9 (2)° respectively (Burns et al, 2012).…”

“…Compound (I) was synthesized following a previously reported procedure (Burns et al, 2012). Dimethylphenylphosphine (11.1 mmol) was added dropwise to a toluene solution (40 ml) of propyl-2-azido-5-methylbenzenesulfonate (9.3 mmol) at 298 K. Effervescence was observed immediately after addition of the phosphine and the clear yellow solution was stirred under N 2 .…”

Development of phosphinimine-sulfonate ligands for late metal catalysis.

“…32 It includes 5 steps: 1) chlorination of the starting toluidine-2-sulfonic acid to its sulfonyl chloride; 2) esterification to form alkyl sulfonates; 3)…”

Phosphinimine zinc complexes and neutral phosphinimines for ring opening polymerization of lactides.

“…The catalytic activity of transition metal catalysts can be controlled by applying proper steric and electronic features around the metal center. In the phosphine sulfonate (PSO) ligands developed by Drent et al, 45 46 Our group has recently reported the synthesis of the palladium complexes and investigated their thermal behavior and ethylene reactivity. 47 In this thesis work, we will discuss the synthesis, characterization and reactivity of tridentate phosphinimine arene sulfonate ligands.…”