One-pot palladium-catalyzed phosphination of aryl iodides with Ph2PSnR3

We found a very efficient one-pot phosphination reaction starting with Ph3P, which by reaction with Na metal in liquid ammonia gives Ph2P- ions that reacted with R3SnCl to afford (trialkylstannyl)diphenylphosphine. The palladium-catalyzed coupling reaction of these stannanes with aryl iodides yield functionalized phosphines in high yield (69-97%). The use of Ph3P as starting reagent, the endurance of the reaction to a wide variety of functional groups and the easiness of a one-pot reaction make this method a useful and versatile approach to tertiary phosphine oxides. (C) 2002 Elsevier Science B.V. All rights reserved.