193277-05-3Relevant academic research and scientific papers
Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst
McAtee, Jesse R.,Krause, Sarah B.,Watson, Donald A.
supporting information, p. 2317 - 2321 (2015/07/27)
Recently we reported a second generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine, for the preparation of allylsilanes using the silyl-Heck reaction. We now show that this new ligand also provides superior reactivity in the preparation of vinylsilanes from styrene derivatives. For the first time, this new ligand provides exceptionally high yields of trialkylvinylsilanes using the widely available palladium pre-catalyst, tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3]. Finally, we demonstrate that this new catalyst system is able to form more highly decorated all-carbon substituted vinylsilanes that have been shown to possess superior reactivity in oxidation and cross-coupling reactions.
The first example of nickel-catalyzed silyl-Heck reactions: Direct activation of silyl triflates without iodide additives
McAtee, Jesse R.,Martin, Sara E.S.,Cinderella, Andrew P.,Reid, William B.,Johnson, Keywan A.,Watson, Donald A.
, p. 4250 - 4256 (2014/06/09)
For the first time, nickel-catalyzed silyl-Heck reactions are reported. Using simple phosphine-supported nickel catalysts, direct activation of silyl triflates has been achieved. These results contrast earlier palladium-catalyzed systems, which require io
Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: A silyl-heck reaction
McAtee, Jesse R.,Martin, Sara E. S.,Ahneman, Derek T.,Johnson, Keywan A.,Watson, Donald A.
supporting information; experimental part, p. 3663 - 3667 (2012/05/20)
Installing silicon is easy! A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes is reported. This method allows facile conversion of styrenes to E-β-silyl styrenes by using iodotrimethylsilane (TMSI) or chlorotrimethylsilane/lithium iodide (see scheme). Terminal allyl silanes with good E/Z ratios are also readily accessed from α-olefins.
Aromatic β-silylethenylation reactions via organogallium compounds
Kido, Yoshiyuki,Yoshimura, Satoru,Yamaguchi, Masahiko,Uchimaru, Tadafumi
, p. 1445 - 1458 (2007/10/03)
In the presence of GaCl3, silylethyne reacted electrophilically with aromatic hydrocarbons to give β-silylethenylated arenes. The reaction proceeded via cationic species generated by the interaction of GaCl3 and silylethyne. High reactivity of the intermediate was demonstrated by the rapid reaction rate at -78 °C using close to the equimolar amount of the substrates. ipso-Substitution reaction took place with 1,2,3- trimethoxybenzene. Structures and properties of several organogallium compounds involved in the reactions are discussed.
