61077-65-4

Upstream product

• 96-09-3 styrene oxide 
• 1802-55-7 diallylzinc 
• 122-78-1 phenylacetaldehyde 
• 762-72-1 allyl-trimethyl-silane 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 104747-24-2 (vinyl)Cu*BF₃ 
• 917-57-7 vinyllithium 
• 1730-25-2 allylmagnesium bromide 
• 2622-05-1 allylmagnesium bromide 
• 591-87-7 Allyl acetate 
• 7393-43-3 tetraallyl tin 
• 100-42-5 styrene 
• 2551-83-9 allyltrimethoxysilane 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 81096-91-5 (±)-4-phenylbutane-1,3-diol 
• 1218948-44-7 C₁₁H₁₃Cl₂O₂P 
• 1374151-76-4 1-(oxiran-2-yl)-3-phenylpropan-2-ol 
• 1374151-77-5 (1-benzyl-2-oxiran-2-yl)ethoxy-tert-butyldimethylsilane 
• 1374151-79-7 6-(tert-butyldimethylsilyloxy)-7-phenylhept-1-en-4-ol 

Relevant academic research and scientific papers

Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis

The stereospecific reductive cross-electrophile coupling reaction of 2-aryl-4-chlorotetrahydropyrans to afford disubstituted cyclopropanes is reported. This ring contraction presents surprises with respect to the stereochemical outcome of reaction of the

Copper(i) and silver(i) chemistry of vinyltrifluoroborate supported by a bis(pyrazolyl)methane ligand

Although unsaturated organotrifluoroborates are common synthons in metal-organic chemistry, their transition metal complexes have received little attention. [CH2(3,5-(CH3)2Pz)2]Cu(CH2CHBF3), (SIPr)Cu(MeCN)(CH2CHBF3) and [CH2(3,5-(CH3)2Pz)2]Ag(CH2CHBF3) represent rare, isolable molecules featuring a vinyltrifluoroborate ligand on coinage metals. The X-ray crystal structures show the presence of three-coordinate metal sites in these complexes. The vinyltrifluoroborate group binds asymmetrically to the metal site in [CH2(3,5-(CH3)2Pz)2]M(CH2CHBF3) (M = Cu, Ag) with relatively closer M-C(H)2distances. The computed structures of [CH2(3,5-(CH3)2Pz)2]M(CH2CHBF3) and M(CH2CHBF3), however, have shorter M-C(H)BF3distances than M-C(H)2. These molecules feature various inter- or intra-molecular contacts involving fluorine of the BF3group, possibly affecting these M-C distances. The binding energies of [CH2CHBF3]?to Cu+, Ag+and Au+have been calculated at the wB97XD/def2-TZVP level of theory, in the presence and absence of the supporting ligand CH2(3,5-(CH3)2Pz)2. The calculation shows that Au+has the strongest binding to the [CH2CHBF3]?ligand, followed by Cu+and Ag+, irrespective of the presence of the supporting ligand. However, in all three metals, the supporting ligand weakens the binding of olefin to the metal. The same trends were also found from the analysis of the σ-donation and π-backbonding interactions between the metal fragment and the π and π* orbitals of [CH2CHBF3]?

Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols

We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates

Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters

In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.

Allylation and propargylation of aldehydes mediated byin situgenerated zinc from the redox couple of Al and ZnCl2in 2N HCl

A simple one pot allylation and propargylation of aldehydes mediated by zinc(0), which isin situgenerated from the redox couple of Al and ZnCl2in 2N HCl, is demonstrated to afford the corresponding homoallyl and homopropargyl alcohols with exce

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.

Indium(I)/CuFe2O4 Reagent for Allylation of Carbonyls and Epoxide Rearranged Carbonyls

Abstract: Indium(I)/CuFe2O4 reagent forcarbonyl allylation and epoxide rearranged carbonyl allylation is proposed forformation of homoallylic alcohols. The In(I) reagent in combination withcatalytic amount of CuFe2O4support in situ formation of nucleophilicallylic indium from allyl halide in THF medium. Nucleophilic allylic indiumspecies react with carbonyls to form homoallyl alcohols in good to excellentyields. Under the presented reaction conditions arylepoxides undergo smoothrearrangement into aldehydes that are also allylated with formation of homoallylalcohols. The process is highly efficient and tolerates different functionalgroups.