352229-41-5Relevant academic research and scientific papers
Asymmetric Hydrosilylation of β-Silyl Styrenes Catalyzed by a Chiral Palladium Complex
He, Yu-Han,Ji, Yang,Li, Rui,Su, Yan,Wang, Yi-Fan
, (2022/02/10)
A palladium complex coordinated with a chiral SIPHOS ligand was evaluated as an efficient catalyst for asymmetric hydrosilylation of β-silyl styrenes with trichlorosilane and 23 1,2-bis(silyl) chiral compounds were produced. Good to excellent enantioselec
Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane via carbene migratory insertion
Mu, Qiu-Chao,Wang, Xing-Ben,Ye, Fei,Sun, Yu-Li,Bai, Xing-Feng,Chen, Jing,Xia, Chun-Gu,Xu, Li-Wen
supporting information, p. 12994 - 12997 (2018/11/23)
The direct olefination of aryl/alkyl halides with trimethylsilyldiazomethane (TMSD) as a C1- or C2-unit was achieved successfully via a metal carbene migratory insertion process, which offered a new access to afford (E)-vinyl silanes and (E)-silyl-substituted α,β-unsaturated amides in good yields and high chemoselectivity.
A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions
Krause, Sarah B.,McAtee, Jesse R.,Yap, Glenn P. A.,Watson, Donald A.
supporting information, p. 5641 - 5644 (2017/10/25)
Studies of the silyl-Heck reaction aimed at identifying active palladium complexes have revealed a new species that is formed in situ. This complex has been identified as the palladium iodide dimer, [(JessePhos)PdI2]2, which has been
Stereoselective peterson olefinations from bench-stable reagents and N-phenyl imines
Das, Manas,Manvar, Atul,Jacolot, Ma?wenn,Blangetti, Marco,Jones, Roderick C.,O'Shea, Donal F.
supporting information, p. 8737 - 8740 (2015/06/08)
The synthesis of bench-stable α,α-bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ～1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N-benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as N,N-bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.
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.
New one-pot synthesis of (E)-β-aryl vinyl halides from styrenes
Pawluc, Piotr,Hreczycho, Grzegorz,Szudkowska, Justyna,Kubicki, Maciej,Marciniec, Bogdan
supporting information; experimental part, p. 3390 - 3393 (2009/12/01)
A new, efficient protocol for the highly stereoselective one-pot synthesis of (E)-β-aryl vinyl iodides and (￡)-β-aryl vinyl bromides from styrenes based on sequential ruthenium-catalyzed silylative coupling-N-halosuccinimide-mediated halodesilylation reactions is reported.
Synthesis of (E)-alkenes via hydroindation of C{triple bond, long}C in InCl3-NaBH4 system
Wang, Chunyan,Yan, Lei,Zheng, Zhiguo,Yang, Deyu,Pan, Yuanjiang
, p. 7712 - 7717 (2007/10/03)
In InCl3-NaBH4-MeCN system, terminal aryl alkynes could couple with aryl iodides and bromides to give disubstituted alkenes via hydroindation of C{triple bond, long}C. In the similar way, (E)-alkenylsilanes were synthesized via reduction of alkynylsilanes in tetrahydrofuran (THF) in high yields. The processes showed high regio- and stereoselectivity.
