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

Article abstract of DOI:10.1016/0022-328X(96)06136-0

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.