75476-56-1

Upstream product

• 617-86-7 triethylsilane 
• 1073-67-2 4-vinylbenzyl chloride 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 873-73-4 4-n-chlorophenylacetylene 

Relevant academic research and scientific papers

Manganese-catalysed divergent silylation of alkenes

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.].

Manganese-Catalyzed Dehydrogenative Silylation of Alkenes following Two Parallel Inner-Sphere Pathways

We report on an additive-free Mn(I)-catalyzed dehydrogenative silylation of terminal alkenes. The most active precatalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate which undergoes rapid Si-H bond cleavage of the silane HSiR3 forming the active 16e- Mn(I) silyl catalyst [Mn(dippe)(CO)2(SiR3)] together with liberated butanal. A broad variety of aromatic and aliphatic alkenes was efficiently and selectively converted into E-vinylsilanes and allylsilanes, respectively, at room temperature. Mechanistic insights are provided based on experimental data and DFT calculations revealing that two parallel reaction pathways are operative: an acceptorless reaction pathway involving dihydrogen release and a pathway requiring an alkene as sacrificial hydrogen acceptor.

Atomically dispersed gold anchored on carbon nitride nanosheets as effective catalyst for regioselective hydrosilylation of alkynes

The hydrosilylation of alkynes is a powerful process for producing vinylsilane compounds, which are synthetically versatile organosilicon reagents in organic chemistry. Herein, atomically dispersed Au anchored on g-C3N4 nanosheets is developed as a superi

[Rh(Cod)Cl]2/Pph3?catalyzed dehydrogenative silylation of styrene derivatives with NBE as a hydrogen acceptor

Direct synthesis of arylalkenylsilanes by [Rh(COD)Cl]2/ PPh3-catalyzed dehydrogenative silylation of styrene derivatives with R3SiH (R = alkyl, alkoxy, aryl) was realized, in which norbornene (NBE) and PPh3 play a key role in achieving excellent selectivity in the formation of dehydrogenative silylation products. Moreover, this high-yielding transformation exhibits a broad substrate scope and good functional group tolerance.

Method for selective preparation of alkenyl silane

A method for realizing selective silylation of terminal olefin by ligand regulation is disclosed. According to the method, terminal olefin and trisubstituted silane, which are used as raw materials, and trifluorotoluene, which is used as a solvent, react

Nickel-Catalyzed Decarboxylative C–Si Bond Formation: A Regioselective Cross-Coupling Between Trialkyl Silanes and α,β-Unsaturated Carboxylic Acids

This report presents the first example of nickel-catalyzed mild decarboxylative cross-coupling reaction for the regioselective formation of C–Si bond. An easily accessible and significantly stable Ni (dmg)2 owes the role of key promoter. This r

FeCl2/DTBP: An efficient and highly E-selective cross - coupling of silanes with styrene and its derivatives

An efficient FeCl2-catalyzed cross-coupling of silanes with styrene and its derivatives using DTBP as oxidant for selective synthesis of vinylsilanes was developed. This method presented an inexpensive, non-toxic and environmentally benign cata

Regio- and stereoselective hydrosilylation of alkynes catalyzed by SiO2 supported Pd-Cu bimetallic nanoparticles

An efficient, recyclable Pd-Cu bimetallic nanoparticle catalyst has been prepared, which exhibits superior activity and selectivity toward the hydrosilylation of internal and terminal alkynes under mild reaction conditions with a low catalyst loading. Distinct enhancement in catalytic performance is observed when compared with traditional monometallic catalysts, and the composition of BMNPs is found to be crucial in both selectivity and yield. This kind of elevation in catalytic performance can be ascribed to the enrichment of active sites (Pd) on the catalyst surface and a phenomenon collectively referred to as "synergistic effects". The successful application of BMNPs as catalysts in the alkyne hydrosilylation opens up new possibilities for the excavation of the value of bimetallic nanoparticles in catalysts' development for sustainable chemistry.

Stereoselective synthesis of vinylsilanes: Via copper-catalyzed silylation of alkenes with silanes

An efficient and stereoselective synthesis of vinylsilanes via copper-catalyzed direct silylation of alkenes with silanes was developed. This study offers a new and expedient strategy for the synthesis of synthetically useful alkenyl organosilicon compoun

Well-defined NHC-rhodium hydroxide complexes as alkene hydrosilylation and dehydrogenative silylation catalysts

Alkene hydrosilylation and dehydrogenative silylation reactions, mediated by [Rh(cod)(NHC)(OH)] complexes (cod = 1,5-cyclooctadiene; NHC = N-heterocyclic carbene) are described. The study details a comparison of the catalytic activity and steric characteristics of four rhodium complexes bearing different NHC ligands. The novel [Rh(cod)(Ii-PrMe)(OH)] complex (Ii-PrMe = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidine) was designed to improve the reactivity of Rh(i)-hydroxides and proved to be a successful promoter of hydrosilylation and dehydrogenative silylation, displaying good stereo- and regiocontrol. The Royal Society of Chemistry 2013.