WATER-SOLUBLE PHOSPHINES .8. PALLADIUM-CATALYZED P-C CROSS-COUPLING REACTIONS BETWEEN PRIMARY OR SECONDARY PHOSPHINES AND FUNCTIONAL ARYLIODIDES - A NOVEL SYNTHETIC ROUTE TO WATER-SOLUBLE PHOSPHINES

Tertiary phosphines Ph(2)P-Ar and PhP(Ar)(2) containing mono- and disu bstituted 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 phe nylphosphine and substituted aryliodides I-C6H4-X or I-C6H3-XY in orga nic solvents (dimethylacetamide, acetonitrile, methanol) using organic amines or potassium and sodium acetate as bases. If the primary phosp hine is employed in the appropriate stoichiometric ratio, functionaliz ed secondary phosphines, e.g. Ph(H)P-C6H4-p-SO3Na, may be obtained sel ectively.