89529-64-6

Upstream product

• 1296846-26-8 1-(4-methoxyphenyl)-3-methyl-1,2-butadiene 
• 84384-30-5 4-(4-methoxyphenyl)-2-methyl-3-butyn-2-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 557-93-7 2-bromoprop-1-ene 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 3017-69-4 2-methyl-1-propenylbromide 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 123-11-5 4-methoxy-benzaldehyde 
• 847661-06-7 2-methylprop-2-ene-1-sulfonyl fluoride 
• 696-62-8 para-iodoanisole 
• 78-79-5 isoprene 
• 943-88-4 4-(p-methoxyphenyl)-3-butene-2-one 

Downstream Products

• 1175163-78-6 1-[(2Z)-5-butyl-3-methylhexa-2,5-dien-1-yl]-4-methoxybenzene 
• 1607822-30-9 6-(4-methoxyphenyl)-4-methyl-2-phenyl-3,6-dihydro-2H-1,2-oxazine 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 

Relevant academic research and scientific papers

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

Diene compound and synthesis method thereof

The invention provides a synthesis method of a diene compound. The method comprises the following steps: taking beta-alkenyl bromide and alpha/beta-alkenyl bromide as raw materials, adding a catalyst, a ligand, a reducing agent, a halogen ion exchanger and a solvent, and carrying out reductive coupling reaction to obtain the required diene compound. The invention further provides a diene compound. The diene compound and the synthetic method thereof provided by the invention have the advantages of green and environment-friendly catalyst metal, low toxicity, high efficiency, low cost, mild reaction, simple operation and high yield.

Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of (E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters

A highly regio-, diastereo-, and enantioselective Diels-Alder reaction of β,γ-unsaturated α-ketoesters with (E)-1-phenyl dienes has been accomplished by using a stable and easily available chiral N,N′-dioxide/zinc(II) complex as catalyst. Only one isomer of the corresponding cyclohexenes with three chiral centers was obtained in good to excellent yields with excellent ee values under mild reaction conditions. The configurations of the product and chiral N,N′-dioxide/zinc(II) catalyst were identified by X-ray diffraction analysis. In addition, a possible catalytic model was proposed to explain the origin of the asymmetric induction.

Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System

A redox neutral rearrangement of an allene to a 1,3-diene by means of a unique palladium hydride complex is reported. The palladium hydride complex is generated from a simple Pd 0 source and boric acid [B(OH) 3 ], which is typically identified as a waste by-product of the Suzuki-Miyaura reaction. A mechanism for this transformation using this novel palladium hydride complex is presented; using a direct sample loop and flow injection ESI-HRMS analysis we have detected and identified key π-allylpalladium complexes that support the addition of the palladium hydride complex to the allene.

Copper-Catalyzed Alkenylation of Alcohols with β-Nitrostyrenes via a Radical Addition-Elimination Process

A new method for the preparation of allylic alcohol derivatives has been developed via a radical mechanism using DTBP as the radical initiator promoted by copper salt. The C(sp3)-H bond in various alcohols, toluene derivatives, and alkanes were successfully converted into C-C bonds to yield the desired products in moderate to good yields.

Catalytic formal [4 + 2] cycloadditions between unactivated allenes and N-hydroxyaniline catalyzed by AuCl3/CuCl2/O2

AuCl3-catalyzed formal [4 + 2]-cycloadditions between substituted allenes and N-hydroxyanilines are described. This reaction sequence comprises initial isomerizations of allenes to butadienes under N2 and subsequent oxidations of N-h

Stereoselective synthesis of 1,3-dienes from propargylic alcohols by LiAlH4/AlCl3

Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction con

Synthesis of dienes by palladium-catalyzed couplings of tosylhydrazones with aryl and alkenyl halides

Two different combinations of coupling partners can be employed for the synthesis of conjugated dienes by palladium-catalyzed cross-coupling with tosylhydrazones: α,β-unsaturated ketone and aryl halide or alkenyl halide and non-conjugated tosylhydrazone. Depending on the substrate, a vinylogous hydride elimination is responsible for the formation of the final dienes. Copyright

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl) silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1,3-(E) and (Z)-dienes. Their (Z)→(E) isomerization by classical means fails or leads to their polymerization. It is shown that SO2 can isomerize 1-aryl-3-methyl-1,3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1,3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)→(E) isomerizations.