22836-25-5Relevant academic research and scientific papers
Nucleophilic phosphanylation of fluoroaromatic compounds with carboxyl, carboxymethyl, and aminomethyl functionalities - An efficient synthetic route to amphiphilic arylphosphanes
Hingst, Martin,Tepper, Michael,Stelzer, Othmar
, p. 73 - 82 (2007/10/03)
Chiral- and multiply-carboxylated phosphanes and phosphanyl derivatives of benzoic and phthalic acids (1-9) are accessible in high yields by nucleophilic phosphanylation of potassium or lithium salts of commercially available fluorobenzoic and 3-fluorophthalic acids with Ph2PH, Ph2PK, PhPLi2, Ph(K)P-(CH2)3-P(K)Ph in superbasic media (DMSO/KOH) or in THF and DME. The hitherto unknown phosphanylphenylacetic acids (10-13) and phosphanylbenzylamines RR′P-C6H4-CH2-NH2 (14-19, R, R′ = H, Me, Ph) with unsubstituted amino groups were also synthesized by this method. The diphenylphosphanyl derivatives 14-16 (R, R′ = Ph) are accessible by an alternative method involving LiAlH4 reduction of the phosphanylbenzonitriles (20-22), which were obtained in high yields by nucleophilic phosphanylation of the corresponding fluoro- or chlorobenzonitriles. The novel bidentate phosphanylbenzonitrile 23 has also been obtained using this synthetic route. All compounds were completely characterized by elemental analysis, NMR spectroscopy, and mass spectrometry.
Water soluble phosphines VIII. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - A novel synthetic route to water soluble phosphines
Herd, Oliver,Hessler, Antonella,Hingst, Martin,Tepper, Michael,Stelzer, Othmar
, p. 69 - 76 (2007/10/03)
Tertiary phosphines Ph2P-Ar and PhP(Ar)2 containing mono-and disubstituted aromatic ring systems Ar (Ar = C6H4-X and C6H3-XY; X, Y = Me, OH, NH2, COOH, COOMe and SO3Na) are accessible in good yields by Pd(0)-catalyzed cross coupling reactions between diphenylphosphine or phenylphosphine and substituted aryliodides I-C6H4-X or I-C6H3-XY in organic solvents (dimethylacetamide, acetonitrile, methanol) using organic amines or potassium and sodium acetate as bases. If the primary phosphine is employed in the appropriate stoichiometric ratio, functionalized secondary phosphines, e.g. Ph(H)P-C6H4-p-SO3Na, may be obtained selectively.
A new synthesis of hydrophilic carboxylated arylphosphines
Ravindar,Hemling,Schumann,Blum
, p. 841 - 851 (2007/10/02)
An efficient synthetic procedure for the preparation of versatile functionally substituted arylphosphines from commercially available starting materials is reported together with alternative routes for (carboxyphenyl)diphenyl phosphines.
