25108-57-0

Upstream product

• 55311-42-7 2-(3-methoxyphenyl)propan-2-ol 
• 108-24-7 acetic anhydride 
• 917-64-6 methyl magnesium iodide 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 51985-06-9 3-hydroxy-alpha-methylstyrene 
• 74-88-4 methyl iodide 
• 10259-22-0 ethyl 3-methoxybenzoate 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 13154-14-8 1-propenylmagnesium bromide 
• 13291-18-4 isopropenylmagnesium bromide 
• 108-22-5 Isopropenyl acetate 
• 2398-37-0 3-methoxyphenyl bromide 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 6380-20-7 3-isopropylanisole 
• 860589-95-3 [1-(3-methoxy-phenyl)-1-methyl-ethyl]-dimethyl-amine 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 29123-95-3 3-(3-methoxyphenyl)-3-buten-1-ol 
• 77939-81-2 C₁₀H₁₃O⁽¹⁺⁾ 
• 98-83-9 isopropenylbenzene 
• 1538-92-7 1-(1-Chloro-1-methyl-ethyl)-3-methoxy-benzene 
• 72527-86-7 5-<2-(3-Methoxyphenyl)-allyl>-8a-methyl-1,6-dioxo-octahydronaphthalin 
• 61364-55-4 4-<2-(3-Methoxyphenyl)-allyl>-7a-methyl-2,3,4,6,7,8-hexahydro-1,5(1H)-indandion 
• 3027-13-2 1-(3-methoxyphenyl)propan-2-one 
• 856345-47-6 3-(α-Dimethylamino-isopropyl)-phenol 
• 1029124-39-7 (E)-1-methoxy-3-(1-nitroprop-1-en-2-yl)benzene 
• 1092399-44-4 (R)-ethyl 2-hydroxy-4-(3-methoxyphenyl)pent-4-enoate 
• 1198746-19-8 (R)-methyl 2-hydroxy-4-(3-methoxyphenyl)-2-(trifluoromethyl)pent-4-enoate 

Relevant academic research and scientific papers

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.

MnBr2 catalyzed regiospecific oxidative Mizoroki-Heck type reaction

Herein, we report an unprecedented regiospecific oxidative Mizoroki-Heck type reaction for the synthesis of ɑ-difluoromethyl homoallylic alcohols. The reaction shows broad substrate scopes and high functional group tolerance. Late-stage functionalization of complex biologically active molecules demonstrates the synthetic potential of this transformation. Mechanistic study supports the involvement of MnBr2 catalyzed radical 1,2-silyl transfer.

Construction of Various Bridged Polycyclic Skeletons by Palladium-Catalyzed Dearomatization

A powerful palladium-catalyzed dearomative cyclization was developed that provides facile access to eight types of bridged tetracyclic skeletons bearing various ring sizes and heterocycles. With this method, several skeletons or analogues of natural products, including tubingensin B and dracaenones, were synthesized. Asymmetric dearomative cyclization enables the construction of various enantiomerically enriched bridged polycyclic systems with up to 99 % ee by employing a chiral palladium catalyst.

Aqueous ZnCl2 Complex Catalyzed Prins Reaction of Silyl Glyoxylates: Access to Functionalized Tertiary α-Silyl Alcohols

An efficient Prins reaction of silyl glyoxylates in the presence of an aqueous ZnCl2 complex as a catalyst was developed, providing functionalized tertiary α-silyl alcohols in high yields under mild conditions. A preliminary investigation indicated that the aqueous ZnCl2 complex acted as a dual functional catalyst of Br?nsted and Lewis acid to activate the carbonyl groups of silyl glyoxylates via a dual-activation model.

An Aliphatic Bischler-Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel-Crafts-type acylation that corresponds to an aliphatic Bischler-Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.

Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes

The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the-OH and-NH2 groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asymmetric version of this reaction was preliminarily investigated.

Palladium/Acid Relay Catalyzed Tandem Heck Coupling/6-Endo Cyclization between ortho-Halogenated Benzoates and Unactivated Terminal Alkenes for the Synthesis of 1-Isochromanones

We report a unique and expeditious route to synthesize 1-isochromanone derivatives through palladium catalyzed tandem Heck coupling/6-endo hydroacyloxylation cyclization between readily available ortho-halogenated benzoates and unactivated alkenes. Various 2-bromo or 2-iodo benzoates can be coupled efficiently with a broad range of alkenes to afford functionalized 1-isochromanones in high yields. Significantly, this cost-efficient and easy-to-handle synthetic methodology will have great prospect application in the synthetic and medicinal chemistry. (Figure presented.).

Oxidative [4+2] Cycloaddition of α-(N-Arylamino) Carbonyls with Aryl Alkenes by Multiple C-H Functionalizations and [1,2]-Aryl Shifts

A new, general copper-catalyzed oxidative tandem [4+2] cycloaddition of α-(N-arylamino) carbonyl compounds with aryl alkenes to produce highly substituted quinolines has been developed, which allows the formation of three new C-C bonds through a sequence of multiple C-H functionalizations, annulation, and [1,2]-aryl shifts.