31641-62-0Relevant articles and documents
Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines
Curran, Dennis P.,Wang, Xiao,Zhang, Qisheng
, p. 3716 - 3719 (2005)
(Equation Presented) The relative reactivities of triphenylphosphine (PPh3) and three fluorous triarylphosphines [(p-RF(CH 2)2C6H4)nPPh 3-n, where n = 1-3] have been compared in internal competition experiments. Product ratios were determined by 31P NMR spectroscopy. The four phosphines have about the same reactivities in oxidation, alkylation, and Staudinger reactions and give comparable yields in a preparative Mitsunobu reaction. Previously observed rate and yield differences in Staudinger reactions of the fluorous phosphines are attributed to solubility effects, not reactivity differences. A light fluorous phosphine [(p-C8F17(CH 2)2C6H4PPh2] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4.
