1032938-01-4Relevant academic research and scientific papers
Oxidative Dehydrogenative Silylation-Alkenation Reaction of Alkyl Aromatics with Silanes
Jiang, Wei,Zhang, Yongxin,Su, Yingpeng,Bao, Xiazhen,Fu, Ying,Huo, Congde
, p. 1065 - 1069 (2020)
A Cu(OAc)2/DDQ/DTBP/Py system catalyzed oxidative dehydrogenative silylation-alkenation tandem reaction of readily available alkyl aromatic compounds with silanes was established. A variety of functionalized alkenyl organosilicon compounds were provided in good to high yields with a total β-(E) selectivity. The control experiments revealed that the transformation might proceed through a radical pathway.
Manganese-catalysed divergent silylation of alkenes
Dong, Jie,Yuan, Xiang-Ai,Yan, Zhongfei,Mu, Liying,Ma, Junyang,Zhu, Chengjian,Xie, Jin
, p. 182 - 190 (2020/12/17)
Transition-metal-catalysed, redox-neutral dehydrosilylation of alkenes is a long-standing challenge in organic synthesis, with current methods suffering from low selectivity and narrow scope. In this study, we report a general and simple method for the manganese-catalysed dehydrosilylation and hydrosilylation of alkenes, with Mn2(CO)10 as a catalyst precursor, by using a ligand-tuned metalloradical reactivity strategy. This enables versatility and controllable selectivity with a 1:1 ratio of alkenes and silanes, and the synthetic robustness and practicality of this method are demonstrated using complex alkenes and light olefins. The selectivity of the reaction has been studied using density functional theory calculations, showing the use of an iPrPNP ligand to favour dehydrosilylation, while a JackiePhos ligand favours hydrosilylation. The reaction is redox-neutral and atom-economical, exhibits a broad substrate scope and excellent functional group tolerance, and is suitable for various synthetic applications on a gram scale. [Figure not available: see fulltext.].
Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Dioxygen initiation
Postigo, Al,Nudelman, Norma Sbarbati
scheme or table, p. 910 - 914 (2011/09/15)
The relevance of radical initiation methodologies for the classical hydrosilylation reactions of organic compounds bearing C-C multiple bonds is due to the need to come up with newer and more efficient methods to effect this reaction, on account of its ap
Vinyl tris(trimethylsilyl)silanes: substrates for Hiyama coupling
Wang, Zhizhong,Pitteloud, Jean-Philippe,Montes, Lucresia,Rapp, Magdalena,Derane, Djenny,Wnuk, Stanislaw F.
, p. 5322 - 5327 (2008/09/21)
The oxidative treatment of vinyl tris(trimethylsilyl)silanes with hydrogen peroxide in aqueous sodium hydroxide in tetrahydrofuran generates reactive silanol or siloxane species that undergo Pd-catalyzed cross-couplings with aryl, heterocyclic, and alkenyl halides in the presence of Pd(PPh3)4 and tetrabutylammonium fluoride. Hydrogen peroxide and base are necessary for the coupling to occur while activation of the silanes with fluoride is not required. The conjugated and unconjugated tris(trimethylsilyl)silanes serve as good cross-coupling substrates. The (E)-silanes undergo coupling with retention of stereochemistry while coupling of (Z)-silanes occurred with lower stereoselectivity to produce an E/Z mixture of products.
