Water soluble phosphines VII. Palladium-catalyzed PC cross coupling reactions between primary or secondary phosphines and functional aryliodides — a novel synthetic route to water soluble phosphines

Abstract Tertiary phosphines Ph 2 OAr and PhP(Ar) 2 containing mono- and disubtituded aromatic ring systems Ar (ArC 6 H 4  and C 6 HXY; X, YMe, OH, NH 2 , COOH, COOMe and SO 3 Na) are accessible in good yields by Pd(O)-catalyzed cross coupling reactions between diphenylphosphine or phenylphosphine and substituted aryliodeds IC 6 H 4 -X or IH 3 -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C 6 H 4 - p -SO 3 Na, may be obtained selectively.