29578-46-9Relevant academic research and scientific papers
N-Acyliminium ion chemistry and palladium catalysis: A useful combination to obtain bicyclic heterocycles
Karstens, Willem F.J.,Klomp, Dirk,Rutjes, Floris P.J.T.,Hiemstra, Henk
, p. 5123 - 5130 (2001)
By using N-acyliminium ion chemistry, several ω-propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an a
Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
Deng, Yuchao,Wei, Xiao-Jing,Wang, Xiao,Sun, Yuhan,No?l, Timothy
, p. 14532 - 14535 (2019/11/21)
Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.
Tethered NHC Ligands for Stereoselective Alkyne Semihydrogenations
Pape, Felix,Teichert, Johannes F.
supporting information, p. 2470 - 2482 (2017/05/22)
A copper(I)-catalyzed semihydrogenation of internal alkynes has been developed. A variety of oxygen- and nitrogen-tethered N-heterocyclic carbene (NHC) complexes have been investigated, leading to a highly Z-selective transformation. The catalyst is generated from inexpensive copper(I) chloride in situ and allows catalytic semihydrogenation down to 10 bar H2.
Propargyltrimethylsilanes as allene equivalents in transition metal-catalyzed [5 + 2] cycloadditions
Wender, Paul A.,Inagaki, Fuyuhiko,Pfaffenbach, Magnus,Stevens, Matthew C.
supporting information, p. 2923 - 2925 (2014/06/23)
Conventional allenes have not been effective π-reactive 2-carbon components in many intermolecular cycloadditions including metal-catalyzed [5 + 2] cycloadditions. We report herein that rhodium-catalyzed [5 + 2] cycloadditions of propargyltrimethylsilanes and vinylcyclopropanes provide, after in situ protodesilylation, a highly efficient route to formal allene cycloadducts. Propargyltrimethylsilanes function as safe, easily handled synthetic equivalents of gaseous allenes and hard-to-access monosubstituted allenes. In this one-flask procedure, they provide cycloadducts of what is formally addition to the more sterically encumbered allene double bond.
ACTION DE SILANES PROPARGYLIQUES SUR DES DERIVES CARBONYLES α-ETHYLENIQUES
Pornet, Jaques,Kolani, N'Baneyape,Mesnard, Danielle,Miginiac, Leone,Jaworski, Krzysztof
, p. 177 - 188 (2007/10/02)
Propargylsilanes RCCCH2Si(CH3)3 easily react with dialkyl alkylidenemalonates, in the presence of TiCl4, to lead to the only product corresponding to an 1,4-addition; the reaction takes place with propargylic rearrangement.
