105535-09-9

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 98-95-3 nitrobenzene 
• 768-56-9 4-Phenylbut-1-ene 
• 208838-30-6 2-bromo-4-(4-nitrophenyl)butane 
• 106-95-6 allyl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 4033-88-9 2-(4-nitrophenyl)malonic acid dimethyl ester 
• 105537-03-9 1-(3,4-dibromobutyl)-4-nitrobenzene 
• 24850-33-7 allyltributylstanane 
• 619-73-8 4-nitrobenzyl chloride 
• 762-72-1 allyl-trimethyl-silane 
• 226570-67-8 (but-3-en-1-yl)zinc(II) bromide 
• 586-78-7 para-nitrophenyl bromide 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 1426853-97-5 (3aR,6R,7S,7aS)-6-(((4-(but-3-en-1-yl)phenyl)amino)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6,7-diol 
• 1426853-99-7 (3aR,5'S,7aR)-3'-(4-(but-3-en-1-yl)phenyl)-2,2-dimethyldihydrospiro[[1,3]dioxolo[4,5-c]pyran-6,5'-oxazolidine]-2',7-(7aH)-dione 
• 105558-47-2 4,4'-di-(3-butenyl)azoxybenzene 

Relevant academic research and scientific papers

Mechanistic studies of an antibody-catalyzed elimination reaction

Catalytic antibody 43D4-3D12, which was generated against the substituted tertiary amine 1, catalyzes the elimination of HF from β- fluoroketone 2. We have cloned and produced the antibody as a chimeric Fab and constructed a model of the active site-substrate complex. Mutagenesis studies of the active site indicate that Glu(H)50 acts as the general base and suggest that Tyr96(L) may also play a role in the elimination reaction. Antibody 43D4-3D12 also efficiently catalyzes the elimination of HBr from substrate 4 by an E2 mechanism, again involving selective abstraction of the proton β-to the nitrophenyl ring by Glu(H)50. The antibody-catalyzed reaction affords predominantly the internal olefins, whereas the major product resulting from the uncatalyzed reaction is the alcohol, which arises from the competing substitution reaction. In addition, antibody 43D43D12 catalyzes an acetal hydrolysis reaction in which Glu(H)50 likely acts as a general acid. These studies point to the Success of this particular hapten design strategy in generating an active site with a desired catalytic functional group. They also illustrate the utility of using related reactions as mechanistic probes of biological catalysis.

In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 ?Csp3 Stille Coupling

Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2-Csp2 cross-coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3-Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross-coupling reaction of an organic halide and an organometallic reagent.

Visible-Light-Mediated Reactions of Electrophilic Radicals with Vinyl and Allyl Trifluoroborates

Visible-light photoredox catalysis enables the vinylation and allylation of electrophilic radicals with readily available potassium trifluoroborate reagents. The processes show good functional group compatibility, and mechanistic and computational studies

Direct allylation of benzyl alcohols, diarylmethanols, and triarylmethanols mediated by XtalFluor-E

We report the direct allylation of benzyl alcohols, diarylmethanols and triarylmethanols mediated by XtalFluor-E using allyltrimethylsilane. The resulting allylated products are obtained in moderate to high yield.

Amine-Activated Iron Catalysis: Air- and Moisture-Stable Alkene and Alkyne Hydrofunctionalization

A simple alkylamine [(iPr)2NEt] has been used to activate an air- and moisture-stable iron(II) pre-catalyst for alkene and alkyne hydrofunctionalization reactions. This amine activation has enabled the highly operationally simple hydrosilylatio

Heterogenisation of ketone catalysts within mesoporous supports for asymmetric epoxidation

The synthesis of the first mesoporous silica (150 A) anchored carbohydrate-derived chiral ketone is described. This new heterogeneous catalyst has been shown to be effective in the asymmetric epoxidation of olefins by oxone. The heterogeneous ketone catalyst has comparable activity to that of its homogeneous counterpart and returned enantioselectivities up to 90% e.e.

Regioselective cross-coupling of allylindium reagents with activated benzylic bromides-a simple and efficient procedure for the synthesis of terminal alkenes

Allylindium reagents undergo facile and highly regioselective cross-coupling with benzylic and cinnamyl bromides in THF at room temperature without any catalyst producing terminal alkenes in high yields. The addition is highly regioselective and is found to provide γ-adducts in all reactions.

Dimethyl malonate as a one-carbon source: A novel method of introducing carbon substituents onto aromatic nitro compounds

A number of carbon substituents possessing various functional groups could be introduced onto aromatic nitro compounds using dimethyl malonate as a one-carbon source and linker. Decarboxylation of both the ester groups originating from dimethyl malonate in this methodology is particularly significant.

Liquid crystals

Compounds of the formula STR1 wherein n stands for the number 0 or 1; the rings A1, A2 and A3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X1 represents a single covalent bond, --COO--, --OOC--, --CH2 CH2 --, p--C6 H4 --, --CH2 CH2 --p-- C6 H4 --, --CH2 CH2 --p--C6 H4 --CH2 CH2 -- or, insofar as the rings A1 and A2 represent 1,4-phenylene, also --NON--; R2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.

Iododediazoniation of Arenediazonium Salts Accompanied by Aryl Radical Ring Closure

Treatment of o-(allyloxy)benzenediazonium tetrafluoroborate (1a) with sodium iodide in acetone affords the cyclized iodide 2a in good yield by a mechanism involving the generation and exo cyclization of the aryl radical 6a.Other diazonium salts (1b-i) containing suitable unsaturated side chains behave similarly, but those (1l,1m) in which there is an N-allylsulfonamido group yield mainly products formed by endo cyclization.The diazonium salts 1j and 1k do not give cyclized products.Factors affecting the mechanism, rates, and regiochemistry of the reaction are discussed.