62056-42-2

Upstream product

• 104-54-1 3-Phenylpropenol 
• 121-69-7 N,N-dimethyl-aniline 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 35552-46-6 <4-Dimethylamino-phenyl>-<2-phenyl-vinyl>-carbinol 
• 103-54-8 cinnamyl acetate 
• 62056-25-1 3-(p-Dimethylaminophenyl)-1-phenylpropylacetat 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 21040-45-9 Cinnamyl acetate 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 300-57-2 allylbenzene 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 

Relevant academic research and scientific papers

Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex

A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.

Method for preparing allyl compound

The invention relates to a method for preparing an allyl compound, and the specific steps are as follows: (1) allyl acetate, a halogenated hydrocarbon, magnesium chips, an additive, a catalyst and a ligand are dissolved in a solvent and mixed, and a crude product is obtained after reaction; and (2) after the crude product obtained in the step (1) is subjected to separation and purification, the allyl compound is obtained. Compared with the prior art, the preparation method effectively avoids the use of a pre-formed organometallic reagent in a traditional synthetic method, and has the characteristics of convenient operation, easy availability of raw materials, low cost, greenness, environmental friendliness and high yield.

Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

An iridium-catalyzed, highly efficient, and site-selective deoxygenation of primary, secondary, and tertiary alcohols has been realized, under the assistance of a 4-(N-substituted amino)aryl directing group. Only the hydroxyl adjacent to the directing group can be deoxygenated. The deoxygenation is performed in water, with formic acid as both the promoter and hydride donor. Excellent yields and functionality tolerance, as well as high efficiency (S/C up to 1000 000, TOF up to 445 000 h-1), are obtained. The kinetic isotope effect studies show that hydride formation is the rate-determining step, and the deoxygenation follows an SN1-type pathway. The deoxygenation protocol has been demonstrated useful in the structural modification of naturally occurring ketones and steroids.

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: The allylation of aryl halides with allylic alcohols

Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

Pincer-Nickel-Catalyzed Allyl-Aryl Coupling between Allyl Methyl Ethers and Arylzinc Chlorides

The P,N,N-pincer nickel complex [Ni(Cl){N(2-Ph2PC6H4)(2′-Me2NC6H4)}]-catalyzed allyl-aryl coupling was studied. The reaction of allyl methyl ethers, including (1-methoxyallyl)arenes and (3-methoxyprop-1-en-1-yl)arenes, with arylzinc chlorides afforded linear (E)-alkenes in high yields, whereas the reaction of (E)-1-methoxytridec-2-ene with p-Me2NC6H4ZnCl generated a mixture of linear and branched alkenes.

Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

Friedel-crafts-type allylation of nitrogen-containing aromatic compounds with allylic alcohols catalyzed by a [Mo3S4Pd(η 3-allyl)] cluster

With the direct use of allylic alcohols as allylating agents, the Friedel-Crafts-type allylic alkylation of nitrogen-containing aromatic compounds catalyzed by a [Mo3S4Pd(η3-allyl)] cluster is achieved. With a 3 mol % catalyst loading in acetonitrile at reflux or 60 °C, a variety of N,N-dialkylanilines and indoles reacted smoothly with allylic alcohols to afford the Friedel-Crafts-type allylation products in good to excellent yields with high levels of regioselectivity.

A transition-metal-free cross-coupling reaction of allylic bromides with aryl- and vinylboronic acids

A cross-coupling reaction between aryl- and vinylboronic acids and various allylic bromides proceeded without the use of a transition-metal catalyst to give the corresponding allylated products in moderate to good yields. The use of an inorganic base (KF

Selective cross-coupling of organic halides with allylic acetates

A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.