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 ...

Related Articles:

Electrochemically supported deoxygenation of epoxides into alkenes in aqueous solution

[Huang, Jing-Mei; Lin, Zhi-Quan; Chen, Dong-Song Organic Letters, 2012 , vol. 14, # 1 p. 22 - 25]

Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl-and 2, 2-Difluorovinyl Tosylates via the Suzuki− Miyaura Cross Coupling

[Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels Journal of Organic Chemistry, 2008 , vol. 73, # 9 p. 3404 - 3410]

New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity

[Journal of the American Chemical Society, , vol. 124, # 35 p. 10278 - 10279]

Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols

[Journal of the American Chemical Society, , vol. 130, # 11 p. 3690 - 3704]

The first examples of rhodium-catalyzed 1, 4-conjugate addition reactions of arylboronic acids with ethenesulfonamides

[Zilaout, Hicham; Van Den Hoogenband, Adri; De Vries, Jelle; Lange, Jos H.M.; Terpstra, Jan Willem Tetrahedron Letters, 2011 , vol. 52, # 45 p. 5934 - 5939]

More Articles...