195324-87-9Relevant articles and documents
Fluorous phosphines and phosphine oxides
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, (2008/06/13)
A method of increasing the fluorous nature of a compound includes the step of reacting the compound with or tagging the compound with at least one of a second compound having the formula: wherein R is an alkyl group or an aryl group, n is 1, 2 or 3 and Rs is a spacer group and Rf is a branched fluorous group. A chemical compound having the general formula: wherein n, Rs and Rf are defined above.
A general method to fluorous ponytail-substituted aromatics
Chen, Weiping,Xu, Lijin,Xiao, Jianliang
, p. 4275 - 4278 (2007/10/03)
Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails.
Thiol additions to acrylates by fluorous mixture synthesis: Relative control of elution order in demixing by the fluorous tag and the thiol substituent
Curran, Dennis P.,Oderaotoshi, Yoji
, p. 5243 - 5253 (2007/10/03)
All possible combinations of a series of three fluorous benzyl tags and three acrylates have been made. The resulting acrylate esters were combined in groups of three (one of each tag) and the resulting mixtures were reacted with a mixture of four thiols under standard conditions to effect conjugate addition. Analysis of the resulting libraries by fluorous hplc showed a primary separation based on the tag and revealed reliable secondary separations based on the thiol and the acrylate. The primary and secondary separations were used together in a preparative 'mixture of mixtures' experiment in which one of the tagged acrylate mixtures was reacted with a mixture of three thiols. The resulting nine component mixture was demixed by fluorous and reverse phase hplc and then detagged to give all nine final products in pure form.
Separation of "light fluorous" reagents and catalysts by fluorous solid-phase extraction: Synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags
Zhang,Luo,Curran
, p. 8866 - 8873 (2007/10/03)
Practical syntheses of new triarylphosphines bearing both linear and branched fluorous tags (Rf) are reported. The phosphines have one, two, or all three aryl rings bearing fluorous tags: (Ph)3-nP(C6H4 (CH2)mRf)n. Fluorous-organic partition coefficients have been measured and the retention properties of both the phosphines and the derived phosphine oxides on fluorous reverse phase silica have been studied. While applications relying on liquid-liquid extractive separations of these phosphines may be limited to those bearing three fluorous chains, the technique of solid phase extraction should be broadly applicable to phosphines, phosphine oxides, and derived metal complexes. A parallel platinum-catalyzed allylation of aldehydes with fluorous allyl stannanes illustrates the usefulness of the new fluorous ligands in small-scale synthesis.
Synthesis of perfluoroalkyl-substituted aryl bromides and their purification over fluorous reverse phase silica
Kainz, Sabine,Luo, Zhiyong,Curran, Dennis P.,Leitner, Walter
, p. 1425 - 1427 (2007/10/03)
(1H,1H,2H,2H-Perfluoroooctyl)-substituted aryl bromides 3a,b were synthesized via copper catalyzed cross-coupling of the iodide 1 with the corresponding arylmagnesium bromides 2a,b. A new, efficient method for the purification of highly fluorinated compounds by column chromatography on fluorous reverse phase silica is also described.
Perfluoroalkyl-substituted arylphosphanes as ligands for homogeneous catalysis in supercritical carbon dioxide
Kainz,Koch,Baumann,Leitner
, p. 1628 - 1630 (2007/10/03)
The solubility of complexes is one decisive factor for their use as homogeneous catalysts in supercritical carbon dioxide (scCO2). Complexes with perfluoroalkyl-substituted arylphosphane ligands (shown schematically on the right), which can be
