94-59-7

Upstream product

• 75-11-6 diiodomethane 
• 1126-61-0 4-allylpyrocatechol 
• 5458-11-7 saffrole dibromide 
• 81372-33-0 5-<1-hydroxy-3-(trimethylsilyl)prop-1-yl>-1,3-benzodioxole 
• 89955-62-4 4R-(-)-illicinone-A 
• 7446-70-0 aluminium trichloride 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 67-64-1 acetone 
• 274-09-9 Methylenedioxybenzene 
• 4873-09-0 allyl tosylate 
• 7228-38-8 5-chloro-1,3-benzodioxole 
• 762-72-1 allyl-trimethyl-silane 
• 120-57-0 piperonal 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 

Downstream Products

• 88855-87-2 5-(benzo[d][1,3]dioxol-5-yl)-7-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 19989-78-7 5-benzo[1,3]dioxol-5-ylmethyl-2-methyl-3-phenyl-isoxazolidine 
• 136612-02-7 3-(4-methoxy)phenyl-4-(3,4-methylenedioxy)benzyl-4,5-dihydroisoxazole 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 74851-88-0 Dimethyl safrole glycol 
• 74851-87-9 5-(2-Methoxy-3-nitrooxy-propyl)-benzo[1,3]dioxole 
• 145134-25-4 2-Methoxymethoxy-4-((E)-propenyl)-phenol 
• 145134-26-5 2-Methoxymethoxy-5-((E)-propenyl)-phenol 
• 41303-44-0 4-[(3,4-methylenedioxy)phenyl]butanoic acid 
• 120802-94-0 5-[(1,3-benzodioxol-5-yl)methyl]-3-(4-methoxyphenyl)-4,5-dihydroisoxazole 
• 120802-92-8 5-[(1,3-benzodioxol-5-yl)methyl]-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole 
• 136612-03-8 4-Benzo[1,3]dioxol-5-ylmethyl-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-isoxazole 
• 33943-26-9 dihydroeugenol acetate 
• 89266-70-6 4-propyl-1,2-phenyl diacetate 

Relevant academic research and scientific papers

Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids

A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones

The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

Palladium-catalyzed tandem isomerization/hydrothiolation of allylarenes

Herein we report a tandem olefin migration/hydrothiolation of allyl benzenes facilitated by an in situ generated palladium hydride. A catalyst system composed of palladium acetate and bidentate ligand dtbpx (1,2-bis(di-tert-butylphosphinomethyl)benzene in the presence of catalytic amounts of triflic acid led to the tandem transformation, which furnished benzylic thioethers. The reaction exhibits high regioselectivity and can be conducted under mild conditions. The robustness of the catalyst is displayed through reactions with coordinating thiols.

Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis

A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.

Flow Metal-Free Ar-C Bond Formation via Photogenerated Phenyl Cations

A convenient photochemical flow protocol for the formation of aryl-carbon bonds via photogenerated phenyl cations has been developed. A wide range of phenylated products, including biaryls, allylarenes, 2-arylacetals and benzyl γ-lactones, was smoothly synthesized in satisfactory yields under metal-free conditions. The adoption of a flow reactor often allowed us to adopt higher concentrations of substrates and shorter irradiation times compared to those usually employed in batch systems.

Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)2Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.

Palladium-catalyzed aerobic oxidative double allylic C-H oxygenation of alkenes: A novel and straightforward route to α,β-unsaturated esters

A mild tandem oxidative functionalization of allyl aromatic hydrocarbons was accomplished using the catalytic system of Pd(OAc)2/DMA under 1 atm O2. The green twofold C-O bond formation involving double allylic C-H oxygenation unlocks opportunities for markedly different synthetic strategies. Moreover, the reaction affords aryl α,β-unsaturated esters directly from readily available terminal olefins in moderate to good yields with excellent chemo- and stereoselectivities.

Trifluoromethylchlorosulfonylation of alkenes: Evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst

Abstract A visible-light-mediated procedure for the unprecedented trifluoromethylchlorosulfonylation of unactivated alkenes is presented. It uses [Cu(dap)2]Cl as catalyst, and contrasts with [Ru(bpy)3]Cl2, [Ir(ppy)2(dtbbpy)]PF6, or eosin Y that exclusively give rise to trifluoromethylchlorination of the same alkenes. It is assumed that [Cu(dap)2]Cl plays a dual role, that is, acting both as an electron transfer reagent as well as coordinating the reactants in the bond forming processes. Double role: The trifluoromethylchlorosulfonylation of unactivated alkenes was developed using [Cu(dap)2]Cl as catalyst (dap=2,9-bis(para-anisyl)-1,10-phenanthroline). [Cu(dap)2]Cl plays a dual role; acting as an electron transfer reagent as well as coordinating the reactants in the bond forming processes.

Biphilic organophosphorus catalysis: Regioselective reductive transposition of allylic bromides via PIII/PV redox cycling

We report that a regioselective reductive transposition of primary allylic bromides is catalyzed by a biphilic organophosphorus (phosphetane) catalyst. Spectroscopic evidence supports the formation of a pentacoordinate (σ5-P) hydridophosphorane as a key reactive intermediate. Kinetics experiments and computational modeling are consistent with a unimolecular decomposition of the σ5-P hydridophosphorane via a concerted cyclic transition structure that delivers the observed allylic transposition and completes a novel PIII/PV redox catalytic cycle. These results broaden the growing repertoire of reactions catalyzed within the PIII/PV redox couple and suggest additional opportunities for organophosphorus catalysis in a biphilic mode.

Environment-friendly, mild and one-step synthesis of Safrole

One-step synthesis of safrole, an important flavor compound, was described. Safrole was prepared by Friedel-Crafts reaction of 1,2-methylenedioxybenzene and allyl alcohol with recyclable Catalysts-Nafion-H. Safrole was obtained with a yield of 80 % and little isosafrole was obtained. The catalyst and excess raw material can be recycled and reused.