Palladium-catalyzed cross-coupling reactions resulting in carbon-carbon bond formation are among the most important organometallic transformations. Palladium-phosphinous acid catalysts are especially appealing because they combine high catalytic activity and high stability to air and water. In this thesis, it was was discovered that palladium-phosphinous acids can promote several cross-coupling reactions such as Stille, Suzuki, Hiyama and Sonogashira reactions of aryl halides including electron-rich aryl chlorides. Some of these reactions were found to proceed in organic solvents and in pure water with high yields which provides new venues for effective recycling of the hydrophilic catalyst.

A mild procedure for one-step oxidative esterification of aldehydes catalyzed by a palladium-phosphinous acid was developed. This reaction is applicable to a range of aliphatic and aromatic substrates and is likely to prove invaluable to the synthesis of multifunctional compounds bearing ester groups. Palladium-phosphinous acids have also been successfully employed in microwave-assisted conjugate addition of arylsiloxanes to unsaturated compounds.