57015-16-4

Upstream product

• 555-31-7 aluminum isopropoxide 
• 7474-65-9 (E)-2-phenylchalcone 
• 591-50-4 iodobenzene 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 925-90-6 ethylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 501-65-5 diphenyl acetylene 
• 119379-68-9 (E)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene 
• 17049-50-2 n-decyl magnesium bromide 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 451-40-1 phenyl benzyl ketone 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 57015-17-5 (Z)-1,2,3-triphenyl-prop-2-en-1-ol 

Downstream Products

• 59405-88-8 (+/-)-3-acetoxy-1t.2.3-triphenyl-propene-⁽¹⁾ 
• 4842-45-9 1,2,3-triphenylpropan-1-one 
• 34987-62-7 1,2-Diphenyl-indan 
• 261171-07-7 (E)-3-bromo-1,2,3-triphenyl-1-propene 
• 18636-54-9 1,2-diphenyl-1H-indene 
• 261171-05-5 (E)-3-azido-1,2,3-triphenyl-1-propene 
• 59405-90-2 (+/-)-3-methoxy-1t.2.3-triphenyl-propene-⁽¹⁾ 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization-Dynamic Kinetic Resolution Cascade

Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high

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.

Nickel-Catalyzed Reductive Coupling of Aldehydes with Alkynes Mediated by Alcohol?

A nickel-catalyzed reductive coupling of aldehydes with alkynes using 1-phenylethanol as reducing agent has been developed. The key achievement of this work is that we demonstrate environmentally benign 1-phenylethanol can serve as a viable alternative reducing agent to Et3B, ZnEt2 and R3SiH for the nickel-catalyzed reductive coupling reaction of aldehyde and alkynes.

Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors

Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.

Iron-catalyzed chemo- and stereoselective hydromagnesiation of diarylalkynes and diynes

Diarylalkynes are chemo- and stereoselectively hydromagnesiated in high yields at room temperature with an iron species generated in situ from FeCl 2and EtMgBr. Functional groups such as bromide, iodide, amine, phenoxide, and alkene are well tolerated. Under similar conditions, diynes are chemo-, regio-, and stereoselectively hydromagnesiated. The resulting alkenylmagnesium compounds are a platform for further functionalization as a one-pot reaction.

Activation of vinyl iodides for the highly enantioselective addition to aldehydes

(Chemical Equation Presented) Mild and tolerant: Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt2 under mild reaction conditions. The compound (S)-1 was found to catalyze the addition of the vinylzinc reag

Nickel(0)-catalyzed formation of oxaaluminacyclopentenes via an oxanickelacyclopentene key intermediate: Me2AlOTf-assisted oxidative cyclization of an aldehyde and an alkyne with nickel(0)

The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined

A novel reaction of titanacyclopentenes and aldehydes with or without Lewis acids

Oxatitanacyclopentenes were prepared in high yields from the reaction of aldehydes with titanacyclopenetens via substitution of ethylene. No insertion product was obtained in this reaction. The combination of alkynes and aldehydes played an important role in the successive formation of oxatitanacyclopentenes. Some oxatitanacyclopentenes are very stable and can be purified using column chromatography. The cooperation between Ti and LA led to very different results from that between Zr and LA.

Reactions of unsaturated azides, 12[≠] azido-1,2,3-triphenylpropenes of varying stabilities: A corrigendum of structure assignment

A reinvestigation of the reaction between 2,3-diphenyl-2-H-azirine (1) and phenyldiazomethane (2) has shown that a literature report has to be corrected since no vinyl azide 4 but rather the allylic compound 3-azido- 1,2,3-triphenyl-1-propene (3) is produced. This stable substance, which can also be prepared by substitution reactions of allylic bromide (E)-10 or from alcohol (E)-11, may be separated into its geometrical isomers (E)-3 and (Z)- 3, although these equilibrate through rapid [3,3] sigmatropic migration of the azido group. Attempts to synthesize 4 by dehydration of azido alcohols 7 using methanesulfonyl chloride and sulfur dioxide or by elimination of hydrogen chloride from azides 15 led only to 3 and 2-benzyl-2,3-diphenyl-2H- azirine (14). This heterocycle, which can also be prepared by Neber rearrangement, has been found to be the thermal and photochemical decomposition product of the unstable vinyl azides 4. However, dehydrations of 7 using thionyl chloride at low temperature have led to the first isolation of 1-azido-1,2,3-triphenyl-1-propenes (4). Starting with 3 and various other allylic azides, rearrangement reactions involving sigmatropic shift of the azido group or photochemical cis-trans isomerization have been investigated, as have base-catalyzed (prototropic) rearrangements to give vinyl azides.

THE-PALLADIUM-CATALYSED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS: A ROUTE TO γ,γ-DIARYL ALLYLIC ALCOHOLS

The reaction of aryl iodides with ethynyl and arylethynyl, dialkyl carbinols in the presence of the tri- or dialkylammonium formate-palladium reagent provides a convenient route to γ,γ-diarylallylic alcohols.In the presence of arylethynyl, alkylcarbinols a lack of regioselectivity was observed and mixtures of β,γ-, γ,γ-diarylallylic alcohols, and α,β-unsaturated ketones were obtained.