76711-42-7

Basic information

• Product Name: (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene
• Synonyms: (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene
• CAS NO: 76711-42-7
• Molecular Weight: 206.36
• Mol File: 76711-42-7.mol

Chemical Properties

• CAS DataBase Reference: (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene(76711-42-7)
• EPA Substance Registry System: (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene(76711-42-7)

Safety Data

• Hazardous Substances Data: 76711-42-7(Hazardous Substances Data)

Upstream product

• 696-62-8 para-iodoanisole 
• 754-05-2 ethenyltrimethylsilane 
• 336193-48-7 2-chloro-1-(4-methoxy-phenyl)-2-trimethylsilanyl-ethanol 
• 637-69-4 4-Methoxystyrene 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 123-11-5 4-methoxy-benzaldehyde 
• 1068-69-5 Tris(trimethylsilyl)methane 
• 1613-96-3 N-(4-methoxybenzylidene)aniline 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 22145-09-1 (1E,3E)-1,4-bis(4-methoxyphenyl)buta-1,3-diene 
• 89510-55-4 1-p-nitrophenyl-4-p-nitrophenylbuta-1E,3E-diene 
• 136795-71-6 (1E,3E)-1-(4-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene 
• 4842-77-7 (2E,4E)-5-(4-methoxyphenyl)-1-phenylpenta-2,4-dien-1-one 
• 65682-02-2 (2E,4E)-1,6-diphenyl-2,4-hexadiene-1,6-dione 
• 1428963-19-2 (1E,3E)-1-(4-methoxyphenyl)-4-(3,5-difluorophenyl)-1,3-butadiene 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 5043-91-4 (E)-4-chloro-4'-methoxystilbene 
• 1104997-33-2 (E)-1-(4-methoxyphenyl)-3,3-diphenyl-1-propene 
• 136618-41-2 E-2'-p-methoxystyryl iodide 

Relevant articles and documents

Asymmetric Hydrosilylation of β-Silyl Styrenes Catalyzed by a Chiral Palladium Complex

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

Nickel-Catalyzed Enantioselective α-Alkenylation of N-Sulfonyl Amines: Modular Access to Chiral α-Branched Amines

Chiral α-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective α-Alkenylation of readily available linear N-sulfonyl amines with alkynes to afford a wide variety of allylic amines without the need for exogenous oxidants, reductants, or activating reagents. The method provides a platform for constructing chiral α-branched amines as well as derivatives such as α-Amino amides and β-Amino alcohols, which can be conveniently accessed from the newly introduced alkene. Given the generality, versatility, and high atom economy of this method, we anticipate that it will have broad synthetic utility.

Synthesis of multinuclear Rh(I) complexes bearing triazolylidenes and their application in C-C and c-Si bond forming reactions

Multidentate carbene ligands are valuable frameworks for the preparation of carbene complexes displaying higher nuclearity. In the present work, we report the synthesis of a series of mono- to tetra-[Rh(COD)I] complexes (3a- d) supported by mesoionic triazol-5-ylidenes. The general synthetic procedure involves the one step reaction of the appropriate triazolium (2a-d) salt in the presence of KHMDS and stoiquiometric amounts of the rhodium(I) precursor. Treatment of complexes 3a-d with an excess of carbon monoxide allows for the quantitative preparation of complexes 4a-d featuring a [Rh(CO)2I] fragment used for the detemination of the donor properties of the new triazolylidene ligands. All complexes have been fully characterized by means of 1H and 13C NMR spectroscopy, melting point, elemental analysis, and in the case of complex 3a, by X-ray crystallography. Comparison of the catalytic activity of the new rhodium complexes in C-C and C-Si bond forming processes demonstrate the enhanced performance of the tetranuclear species suggesting the possibility of strong cooperative effects in these multinuclear complexes.

Build-up of double carbohelicenes using nitroarenes: Dual role of the nitro functionality as an activating and leaving group

The construction of double carbohelicenes is highly fascinating yet challenging work. Disclosed herein is a streamlined and simplified synthetic route to double carbohelicenes starting from nitroarenes through sequential nitro-activated ortho-C-H arylation, denitrative alkenylation and intramolecular cyclodehydrogenation. In this synthetic strategy, the nitro group plays a dual role namely as a leaving group for the denitrative alkenylation and as an activating group for ortho-C-H arylation, which is distinct from those of aryl halides in a conventional coupling reaction. In this work, the palladium-catalyzed Heck-type alkenylation of nitroarenes has been presented, in which the conventionally inert Ar-NO2 bond is cleaved. This work provides a novel synthetic strategy for polycyclic aromatic hydrocarbons (PAHs). This journal is

Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and mechanistic investigations

Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at ?5 ?C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 ?C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.

Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane via carbene migratory insertion

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

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

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

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

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