85260-63-5

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 18178-59-1 (E)-1,2-bis(trimethylsilyl)ethene 
• 754-05-2 ethenyltrimethylsilane 
• 10557-68-3 N-nitrosamide of N-(4-nitrophenyl)acetamide 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 617-86-7 triethylsilane 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 4025-75-6 (4-nitrophenyl)methanesulfonyl chloride 
• 58207-97-9 tributyl[(E)-2-trimethylsilylethenyl]stannane 
• 1066-54-2 trimethylsilylacetylene 
• 62943-02-6 1,1,3,3-tetramethyl-1,3-bis[2-(trimethylsilyl)ethenyl]-(E,E)-disiloxane 
• 938-81-8 N-nitrosoacetanilide 
• 20455-07-6 p-nitrophenyl methanesulfonate 

Downstream Products

• 24325-70-0 (E)-4-methyl-4'-nitrostilbene 
• 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 
• 67309-70-0 4-<4-<4-N,N-dimethylaminophenyl>-butadienyl>-nitrobenzene 
• 72033-82-0 trans,trans-1,4-bis(4-methylphenyl)-1,3-butadiene 
• 1428963-17-0 (1E,3E)-1-(4-nitrophenyl)-4-(4'-tolyl)-1,3-butadiene 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 27370-90-7 1-nitro-4-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]benzene 
• 1694-20-8 trans-4-nitrostilbene 
• 22057-84-7 1-(4-nitrophenyl)-1-phenylethylene 

Relevant academic research and scientific papers

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.

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.

Oxidative cross-coupling of vinylsilanes in water

Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push-pull butadienes.

Vinyldisiloxanes: Their synthesis, cross coupling and applications

During the studies towards the development of pentafluorophenyldimethylsilanes as a novel organosilicon cross coupling reagent it was revealed that the active silanolate and the corresponding disiloxane formed rapidly under basic conditions. The discovery that disiloxanes are in equilibrium with the silanolate led to the use of disiloxanes as cross coupling partners under fluoride free conditions. Our previous report focused on the synthesis and base induced cross coupling of aryl substituted vinyldisiloxanes with aryl halides; good yields and selectivities were achieved. As a continuation of our research, studies into the factors which influence the successful outcome of the cross coupling reaction with both alkyl and aryl substituted vinyldisiloxanes were examined and a proposed mechanism discussed. Further investigation into expanding the breadth and diversity of substituted vinyldisiloxanes in cross coupling was explored and applied to the synthesis of unsymmetrical trans-stilbenes and cyclic structures containing the trans-alkene architecture.

Stereospecific Arylation of Alkenylsilanes with Arylpalladium Acetates

Alkenyltrimethylsilanes ((E)- and (Z)-RCH=CHSiMe3: R = H, Ph, n-C6H13 and CH3OCH2) stereospecifically reacted at 40 deg C or room temperature with in situ generated phenylpalladium acetate to produce R(Ph)C=CSiMe3 and RCH=C(Ph)SiMe3 with inversion of their geometry.The arylation of CH2=CHSiMe3 with arylpalladium acetates gave (E)-ArCH=CHSiMe3 (Ar = XPH; X = H, 4-Me, 4-MeO, 4-Br, 4-I, 4-EtOCO, and 4-NO2) in good yields.

Reaction of Diazonium Salts with Transition Metals. Part 11. Palladium-catalyzed Aryldesilylation of Alkenylsilanes by Arenediazonium Salts

Under palladium(0) catalysis, both (E)- and (Z)-RCH=CHSiMe3(R=Rh, 4-MeC6H4, 4-NO2C6H4, n-C6H13, and MeOCH2) were easily aryldesilylated by ArN2X(Ar=Ph, 4-MeC6H4, 4-BrC6H4 and 4-NO2C6H4; X=BF4, PF6, and Cl) to give (E)-RCH=CHAr and RC(Ar)=CH2 as the main products at 25 deg C in acetonitrile. anti- and syn-1,2-Elimination of Pd(0) and Me3Si from the adducts, threo- and erythro-RCH(PdX)CHSiMe3, generated from ArPdX and (E) and (Z)-RCH=CHSiMe3, respectively, are proposed for the formation of (E)-RCH=CHAr from either isomer of RCH=CHSiMe3.

Synthesis of (E)-(2-Arylethenyl)silanes by Palladium-Catalyzed Arylation of Vinylsilanes in the Presence of Silver Nitrate

A series of (E)-trimethyl(2-arylethenyl)silanes 1-16 and (E)-triethoxy(2-arylethenyl)silanes 17 and 18 has been synthesized by palladium-catalyzed arylation of the corresponding vinylsilanes, in the presence of silver nitrate.Apart from enhancing the rate of the reaction, silver nitrate also completely suppresses the desilylation.In the absence of silver salt, under ordinary Heck arylation conditions, styrene derivatives are formed in good yields.A possible mechanistic rationale for the formation of styrenes is discussed.

PALLADIUM-CATALYSED ARYLATION OF VINYLTRIMETHYLSILANE IN THE PRESENCE OF SILVER NITRATE

A series of arylated vinyltrimethylsilanes have been prepared by means of Heck Arylation in the presence of silver nitrate, which serves to suppress the elimination of the silicon group and enhance the reaction rate.

REACTION OF DIAZONIUM SALTS WITH TRANSITION METALS IX. REACTION OF VINYLTRIMETHYLSILANE WITH ARENEDIAZONIUM TETRAFLUOROBORATES UNDER PALLADIUM(0) CATALYSIS

Arenediazonium tetrafluoroborates (ArN2BF4 where Ar = Ph, 4-MeC6H4, 4-BrC6H4, 4-IC6H4 and 4-NO2C6H4) reacted easily with CH2=CHSiMe3 at 25 deg C to give ArCH=CH2, (E)-ArCH=CHSiMe3 and Ar(Me3Si)C=CH2 in excellent yields under palladium(0) catalysis. (E)-ArCH=CHSiMe3 compounds were obtained predominantly and isolated in good yields by using an excess of CH2=CHSiMe3 over ArN2BF4.Protodesilylation of the reaction mixture afforded styrene derivatives.