- Highly fluorous bidentate phosphines
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The reaction of tetrachlorodiphosphines [Cl2P(CH 2)nPCl2; n = 2-4] with fluorous aromatic precursors 4-bromo(perfluorohexyl)benzene and 4-(perfluorohexyl)phenol gave a series of fluorous-tagged diphosphines [(p-C6F13C 6H4)2P(CH2)nP(C 6H4C6F13-p)2; n = 2-4] and a new diphosphonite [(p-C6F13C6H 4O)2P(CH2)3P(OC6H 4C6F13-p)2]. The improved synthesis of 1,3-bis(dichlorophosphino)propane (dcpp), involved the facile chlorination of the corresponding primary phosphine with triphosgene. Fluorinated diimines RN=C(CH3)C(CH3)=NR, where R = p-C6H 4C6F13 or P-C6H4C 8F17 have also been prepared, and were found to be air-stable alternatives to the highly air-sensitive phosphorus-containing ligands. All compounds were characterised by a variety of techniques including NMR, IR, MS and microanalysis. The successful reduction of the phosphine-oxides [(p-C6F13C6H4)2P(O) (CH2)nP(O)(C6H4C6F 13-p)2; n = 2,3] with phenylsilane is also presented. Georg Thieme Verlag Stuttgart.
- Berven, Bradley M.,Koutsantonis, George A.
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experimental part
p. 2626 - 2630
(2009/04/06)
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- Phosphorus(III) ligands in fluorous biphase catalysis
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The synthesis, coordination chemistry and catalytic applications of a series of perfluoroalkyl-substituted phosphorus(III) ligands is illustrated.
- Bhattacharyya, Pravat,Croxtall, Ben,Fawcett, Joanne,Fawcett, John,Gudmunsen, David,Hope, Eric G.,Kemmitt, Ray D.W.,Paige, Danny R.,Russell, David R.,Stuart, Alison M.,Wood, Dan R.W.
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p. 247 - 255
(2007/10/03)
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- Phosphorus(III) ligands with fluorous ponytails
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A series of phosphorus(III) compounds incorporating one or more C6F13 'ponytails' have been prepared as a pool of ligands for coordination and catalytic studies under the fluorous biphase regime. Solubility studies indicate that only ligands with three or more ponytails are preferentially soluble in perfluorocarbon solvents.
- Bhattacharyya, Pravat,Gudmunsen, David,Hope, Eric G.,Kemmitt, Ray D. W.,Paige, Danny R.,Stuart, Alison M.
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p. 3609 - 3612
(2007/10/03)
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- Direct Perfluoroalkylation of Aromatic and Heteroaromatic Compounds with Perfluoroalkanesulfonyl Chlorides Catalysed by a Ruthenium(II) Phosphine Complex
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The perfluoroalkylation of aromatic and heteroaromatic compounds by perfluoroalkanesulfonyl chlorides 1 has been investigated in the presence of a ruthenium(II) phosphine complex.The reaction of compounds 1 with substituted benzenes or thiophenes proceeded smoothly with extrusion of sulfur dioxide at 120 deg C to give corresponding perfluoroalkylated compounds in good yield.No expected perfluoroalkylated product was obtained in the reaction of compounds 1 with pyrrole; however, 1-trimethylsilyl- and 1-triisopropylsilyl-pyrrole were regioselectively perfluoroalkylated at their 2- and 3-position, respectively.
- Kamigata, Nobumasa,Ohtsuka, Takeshi,Fukushima, Takamasa,Yoshida, Masato,Shimizu, Toshio
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p. 1339 - 1346
(2007/10/02)
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