57266-94-1

Upstream product

• 108-86-1 bromobenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 209733-24-4 10-((Z)-2-Phenyl-1-trimethylsilanyl-vinyl)-9-oxa-10-bora-bicyclo[3.3.2]decane 
• 75-77-4 chloro-trimethyl-silane 
• 645-49-8 cis-stilben 
• 501-65-5 diphenyl acetylene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 603-36-1 triphenylantimony 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 18090-43-2 3,6-bis(trimethylsilyl)cyclohexane-1,4-diene 
• 98-86-2 acetophenone 
• 356070-11-6 trimethyl(1-methylcyclohexa-2,5-dienyl)silane 

Downstream Products

• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

Rhodium-catalyzed hydroarylation and -alkenylation of alkynes with silanediols. A crucial role of the hydroxy group for the catalytic reaction

Aryl- and alkenylsilanediols, which possess two hydroxy groups on the silicon atom, undergo the rhodium-catalyzed addition of an organic group on silicon to internal alkynes. Treatment of several internal alkynes with aryl- or alkenylsilanediols in the pr

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond

The construction of C(sp3)-Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si-Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.

Direct and transfer hydrosilylation reactions catalyzed by fully or partially fluorinated triarylboranes: A systematic study

The present survey serves several purposes. Selected electron-deficient boron Lewis acids catalyze the release of hydrosilanes from cyclohexa-2,5-dien-1-yl-substituted silanes. The two-step process consists of a hydride abstraction to generate a silicon-s

Development and application of a direct vinyl lithiation of cis-stilbene and a directed vinyl lithiation of an unsymmetrical cis-stilbene

Equation Presented The vinyl deprotonation of cis-stilbene can be readily achieved using s-BuLi in THF at -25°C. The generated 1-lithio-1,2- diphenylethene undergoes an in situ Z-to-E isomerization, and subsequent reaction with electrophiles results in an efficient stereoselective synthesis of trisubstituted alkenes. A directed vinyl lithiation of the unsymmetrical cis-stilbene 2-styryl-phenyl-carbamic acid tert-butyl ester can be achieved regioselectively, thereby expanding this methodology for further synthetic applications in indole chemistry.

The efficient stereoselective synthesis of Z-vinylsilanes through the Suzuki-Miyaura coupling of Z-(α-silylvinyl)borinates

Air-stable Z-(α-silylvinyl)borinates (2), easily prepared in a hydroboration-oxidation sequence from I provide a particularly effective route to Z-vinylsilanes (3, 59-97%) through Suzuki-Miyaura coupling.

Z-trimethylsilyl styrenes and 1,3-dienes via the Suzuki reaction

Representative vinyl and aryl bromides are cross-coupled, under basic conditions, to Z-α-trimethylsilylvinylboranes with tetrakis(triphenylphosphine)palladium(O) catalyst to provide the corresponding silylated styrenes and 1,3-dienes (40-60%, >98% Z).

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.

STEREOSPECIFIC PHENYLATION OF ALKENYLSILANES WITH PHENYLPALLADIUM ACETATE

(E)- and (Z)-RCH=CHSiMe3 (R= Ph, n-C6H13, CH3OCH2) reacted stereospecifically with Ph-Pd-OAc to give RCH=C(Ph)SiMe3 and R(Ph)C=CHSiMe3 with inversion of the starting geometry with respect to R and Me3Si groups.