Mechanistic studies on the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water: The effect of the solvent and NaOH promoter

…, MA Ortuño, C López-Mardomingo…

Index: Gordillo, Alvaro; Ortuno, Manuel A.; Lopez-Mardomingo, Carmen; Lledos, Agusti; Ujaque, Gregori; De Jesus, Ernesto Journal of the American Chemical Society, 2013 , vol. 135, # 37 p. 13749 - 13763

Full Text: HTML

Citation Number: 18

Abstract

The mechanism of the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water has been studied using different catalytic precursors. The NaOH promoter converts the initial vinylalkoxysilane into a highly reactive water-soluble vinylsilanolate species. Similarly, deuterium-labeling experiments have shown that, irrespective of the catalytic precursor used, vinylation occurs exclusively at the CH vinylic functionality via a Heck reaction and ...