Pentafluorophenyl diphenylphosphinate

In addition to the most common methods for cyclization of linear peptides (vide supra), alternative coupling reagents have been used with varying success such as BOP-Cl, 140-142 norborn-5-ene-2,3-dicarboximido diphenyl phosphate (NDPP),119-143-144 pentafluorophenyl diphenylphosphinate (FDPP),1145-148 diethyl phosphorocyanidate (DEPC), 138-149 or T3P.197-1501... 

Fig. 9.11. Reaction microarrays in high-throughput ee determination [28]. Reagents and conditions step 1, BocHNCH(R)CC>2H, PyAOP, iPi NEt, DMF step 2, AC2O, pyridine step 3,10% CF3CO2H and 10% Et3SiH in CH2CI2, then 3% Et3N in CH2CI2 step 4, pentafluorophenyl diphenylphosphinate, rPi NEt, 1 1 mixtme of die two fluorescent proline derivatives, DMF, —20°C.

Chen S, Xu J. Pentafluorophenyl diphenylphosphinate anew efficient coupling reagent in pepetide. Tetrahedron Lett. 1991 32 6711-6714. 

A New and Efficient Derivative of Pentafluoro-phenol Pentafluorophenol has found many applications in both solution and solid phase peptide syntheses. Diphenylphosphinic mixed anhydrides are also well known in peptide chemistry. A new and efficient reagent has been prepared from these precursors pentafluorophenyl diphenylphosphinate (FDPP 6) which can be used directly as a coupling reagent without side reactions. FDPP is prepared from mixing equimolar amounts of Diphenylphosphinic Chloride, pentafluorophenol (1), and Imidazole in CH2CI2 at room temperature (eq 3). ... 

M. N., Jones, P.G. and Erdhruegger, C.F. (1989) (Diphenylphosphinomethyl) diphenylphosphine sulfide (Ph2PCH2PPh2S) and its methanide anion Ph2PCHPPh2S- as ligands in organogold chemistry. X-ray crystal structure of [(diphenylphosphino) (diphenylthiophosphinoyl)methanido-P, S]his(pentafluorophenyl)gold(l 11). 

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