Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine‐Based Palladacycle
Balaram S. Takale, Ruchita R. Thakore, Gianluca Casotti, Xaiohan Li, Fabrice Gallou, Bruce H. Lipshutz
Abstract
An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500-1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.
Topics & Concepts
Stille reactionTriphenylphosphineArylCatalysisHalideChemistryNanoreactorAqueous solutionAqueous mediumOrganic chemistryCombinatorial chemistryMedicinal chemistryPolymer chemistryAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions