Synthesis and properties of a novel family of fluorous triphenylphosphine derivatives

被引:83
作者
Richter, B
de Wolf, E
van Koten, G
Deelman, BJ
机构
[1] Univ Utrecht, Debye Inst, Dept Met Mediated Synth, NL-3584 CH Utrecht, Netherlands
[2] Elf Atochem Vlissingen BV, NL-4380 AB Vlissingen, Netherlands
关键词
D O I
10.1021/jo991548v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel approach to the preparation of perfluorotail-functionalized triarylphosphines using a p-silyl substituent as the branching point has been developed. This approach enabled the attachment of between three and nine perfluarotails per phosphorus atom, resulting in the production of highly fluorous tris [p-(1H,1H,2H,2H-perfluoroalkylsilyl)aryl] phosphines, P[C6H4-p-SiMe3-n(CH2CH2CxF2x+1)(n)](3) (n = 1, 2, 3; x = 6, 8), containing between 50 and 67 wt % nuorine. P-31 NMR studies indicate that the phosphorus atoms, and consequently the a-donor and pi-acceptor properties of these phosphines, are not influenced by the electron-withdrawing perfluoroalkyltails. The fluorous triarylphosphines are readily soluble in fluorous solvents and display fluorous phase preference in several fluorous biphasic systems. The phase partitioning of these fluorous ligands, as well as their donor properties, is discussed in relation to their potential for fluorous biphasic catalyst separation.
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页码:3885 / 3893
页数:9
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