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Denmark, Scott E.; Regens, Christopher S.
Tetrahedron letters, 04/2011, Letnik: 52, Številka: 17Journal Article
The development of an effective protocol for the palladium-catalyzed cross-coupling of ( E)-alkenylsilanols with aryl triflates is described. A critical component in the optimization of this method was balancing the stability and reactivity of the triflates in the presence of a nucleophilic promoter. This report highlights the use of a slightly soluble Brønsted base promoter that allows for a low, steady-state concentration of alkenyl(dimethyl)silanolate in solution, thus facilitating cross-coupling in preference to S–O bond cleavage of the triflate.
