42478-41-1

Upstream product

• 18276-17-0 (α-bromovinyl)triethylsilane 
• 617-86-7 triethylsilane 
• 536-74-3 phenylacetylene 
• 16881-77-9 (dimethoxy)methylsilane 
• 1112-54-5 vinyltriethylsilane 
• 888854-17-9 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene 

Downstream Products

• 110163-89-8 (Z)-prop-2-ene-1,1,3-triyltribenzene 
• 98-86-2 acetophenone 
• 2699-87-8 1,2-diphenyl-2-propen-1-ol 
• 13041-70-8 (E)-4-bromostilbene 
• 1694-20-8 trans-4-nitrostilbene 
• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

Engineering regioselectivity in the hydrosilylation of alkynes using heterobimetallic dual-functional hybrid catalysts

The synthesis and characterization of carbon black supported rhodium and iridium heterobimetallic catalysts, termed hybrid catalysts, and their application in the hydrosilylation of alkynes is described. An aryl diazonium grafting procedure was applied to

Markovnikov Hydrosilylation of Alkynes with Tertiary Silanes Catalyzed by Dinuclear Cobalt Carbonyl Complexes with NHC Ligation

Metal-catalyzed hydrosilylation of alkynes is an ideal atom-economic method to prepare vinylsilanes that are useful reagents in the organic synthesis and silicone industry. Although great success has been made in the preparation of β-vinylsilanes by metal-catalyzed hydrosilylation reactions of alkynes, reported metal-catalyzed reactions for the synthesis of α-vinylsilanes suffer from narrow substrate scope and/or poor selectivity. Herein, we present selective Markovnikov hydrosilylation reactions of terminal alkynes with tertiary silanes using a dicobalt carbonyl N-heterocyclic carbene (NHC) complex [(IPr)2Co2(CO)6] (IPr = 1,3-di(2,6-diisopropylphenyl)imidazol-2-ylidene) as catalyst. This cobalt catalyst effects the hydrosilylation of both alkyl- and aryl-substituted terminal alkynes with a variety of tertiary silanes with good functional group compatibility, furnishing α-vinylsilanes with high yields and high α/β selectivity. Mechanistic study revealed that the stoichiometric reactions of [(IPr)2Co2(CO)6] with PhCCH and HSiEt3 can furnish the dinuclear cobalt alkyne and mononuclear cobalt silyl complexes [(IPr)(CO)2Co(μ-ν2:ν2-HCCPh)Co(CO)3], [(IPr)(CO)2Co(μ- ν2:ν2-HCCPh)Co(CO)2(IPr)], and [(IPr)Co(CO)3(SiEt3)], respectively. Both dicobalt bridging alkyne complexes can react with HSiEt3 to yield α-triethylsilyl styrene and effect the catalytic Markovnikov hydrosilylation reaction. However, the mono(NHC) dicobalt complex [(IPr)(CO)2Co(μ- ν2:ν2-HCCPh)Co(CO)3] exhibits higher catalytic activity over the di(NHC)-dicobalt complexes. The cobalt silyl complex [(IPr)Co(CO)3(SiEt3)] is ineffective in catalyzing the hydrosilylation reaction. Deuterium labeling experiments with PhCCD and DSiEt3 indicates the syn-addition nature of the hydrosilylation reaction. The absence of deuterium scrambling in the hydrosilylation products formed from the catalytic reaction of PhCCH with a mixture of DSiEt3 and HSi(OEt)3 hints that mononuclear cobalt species are less likely the in-cycle species. These observations, in addition to the evident of nonsymmetric Co2C2-butterfly core in the structure of [(IPr)(CO)2Co(μ- ν2:ν2-HCCPh)Co(CO)3], point out that mono(IPr)-dicobalt species are the genuine catalysts for the cobalt-catalyzed hydrosilylation reaction and that the high α selectivity of the catalytic system originates from the joint play of the dicobalt carbonyl species to coordinate alkynes in the Co(μ- ν2:ν2-HCCR′)Co mode and the steric demanding nature of IPr ligand.

Rh(I)/(III)-N-Heterocyclic Carbene Complexes: Effect of Steric Confinement Upon Immobilization on Regio- and Stereoselectivity in the Hydrosilylation of Alkynes

Rh(I) NHC and Rh(III) Cp* NHC complexes (Cp=pentamethylcyclopentadienyl, NHC=N-heterocyclic carbene=pyrid-2-ylimidazol-2-ylidene (Py?Im), thiophen-2-ylimidazol-2-ylidene) are presented. Selected catalysts were selectively immobilized inside the mesopores

Carbon supported hybrid catalysts for controlled product selectivity in the hydrosilylation of alkynes

A series of Rh- and Ir-hybrid catalysts with varying tether lengths has been prepared by immobilization of RhI, RhIIIand IrIIIcomplexes on carbon blackviaradical grafting. The performance of the different catalysts was ass

Synthesis and structure of thienyl Fischer carbene complexes of PtIIfor application in alkyne hydrosilylation

Transmetallation of group 6 thienylene Fischer carbene complexes to PtIIprecursors yielded new examples of neutral platinum(ii) bisethoxycarbene complexes with either 2-thienyl (T) or 5-thieno[2,3-b]thienylene (TT) carbene substituents. The use

Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications

Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.

Short-chained platinum complex catalyzed hydrosilylation under thermomorphic conditions: Heterogeneous phase separation at ice temperature

Homogeneous catalysts PtCl2 [5,5′-bis-(n-ClCF2 (CF2 )3 CH2 OCH2 )-2,2′-bpy] (2A) and PtCl2 [5,5′-bis-(n-HCF2 (CF2 )3 CH2 OCH2 )-2,2′-bpy] (2B), which contained short fluorous chains, were synthe-sized and used in catalysis of hydrosilylation of alkynes. In these reactions the thermomorphic mode was effectively used to recover these catalysts from the reaction mixture up to eight cycles by taking advantage of heterogeneous phase separation at ice temperature. This kind of catalysis had previously been observed in fluorous catalysts of platinum containing about 50% F-content, but in this work the percentage of F-content is decreased to only about 30%, by which we termed them as “very light fluorous”. Our new type of catalyst with limited number of F-content is considered as the important discovery in the fluorous technology field as the reduced number of fluorine atoms will help to be able to comply the EPA 8-carbon rule. The metal leaching after the reaction has been examined by ICP-MS, and the testing results show the leaching of residual metal to be minimal. Additionally, comparing these results to our previous work, fluorous chain assisted selectivity has been observed when different fluorous chain lengths of the catalysts are used. It has been found that there exists fluorous chain assisted better selectivity towards β-(E) form in the Pt-catalyzed hydrosilylation of non-symmetric terminal alkyne when the Pt catalyst contains short fluorous chain (i.e., 4 Cs). Phenyl acetylenes showed the opposite regioselectivity due to pi-pi interaction while using the same catalyst via Markovnikov’s addition to form terminal vinyl silane, which is then a major product for Pt-catalyzed hydrosilylation of terminal aryl acetylene with triethylsilane. Finally, the kinetic studies indicate that the insertion of alkyne into the Pt-H bond is the rate-determining step.

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

A Platinum Molecular Complex Immobilised on the Surface of Graphene as Active Catalyst in Alkyne Hydrosilylation

A platinum complex bearing a N-heterocyclic carbene (NHC) ligand functionalised with a pyrene-tag is immobilised onto the surface of reduced graphene oxide (rGO). The hybrid material composed of an organometallic complex and a graphene derivative is ready

Dichloro(ethylenediamine)platinum(II), a water-soluble analog of the antitumor cisplatin, as a heterogeneous catalyst for a stereoselective hydrosilylation of alkynes under neat conditions

A stereoselective method for the hydrosilylation of internal and terminal alkynes under heterogeneous catalysis by dichloro(ethylenediamine)platinum(II) is discussed. This commercially available platinum complex operates under neat conditions at 90 °C, pr