485844-19-7

Upstream product

• 21040-45-9 Cinnamyl acetate 
• 1765-93-1 4-fluoroboronic acid 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 25776-12-9 sodium tetrakis(4-fluorophenyl)borate 
• 103-54-8 cinnamyl acetate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 4392-24-9 Cinnamyl bromide 
• 2687-12-9 cinnamyl chloride 
• 300-57-2 allylbenzene 
• 2294-43-1 1-allyl-4-bromo-benzene 
• 591-50-4 iodobenzene 

Downstream Products

• 42882-83-7 3-(phenyl)-5-(4-fluorophenyl)-1-p-toluenesulfonyl-1H-pyrazole 

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.

Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents

The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.

Iron-Catalyzed Grignard Cross-Couplings with Allylic Methyl Ethers or Allylic Trimethylsilyl Ethers

We have found that cross-coupling between aryl Grignard reagents and allylic methyl ethers proceeded well in the presence of a catalytic amounts of Fe(acac) 3 to afford the corresponding allylic substitution products in good yields. Under the same conditions, allylic trimethylsilyl ethers also reacted with Grignard reagents to give the corresponding cross-coupling products.

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

A palladium NNC-pincer complex: An efficient catalyst for allylic arylation at parts per billion levels

Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50°C gave the corresponding arylated products in excellent yields. Total turnover numbers of up to 500 000 000 and turnover frequencies of up to 11 250 000 h-1 were achieved.

Photochemical Heck benzylation of styrenes catalyzed by Na[FeCp(CO)2]

Iron-catalyzed Heck coupling of benzyl chlorides and styrenes proceeds under photochemical conditions using the well-known anionic complex, [FeCp(CO)2]- (Fp-), as a catalyst. The reaction likely proceeds through the established SN2 mechanism for Fp- alkylation, followed by styrene migratory insertion and β-hydride elimination steps that are enabled by photochemical CO dissociation.

A vesicular self-assembled amphiphilic palladium NNC-pincer complex-catalyzed allylic arylation of allyl acetates with sodium tetraarylborates in water

Abstract The allylic arylation of various allyl acetates with sodium tetraarylborates proceeded in water in the presence of a vesicular self-assembled amphiphilic palladium NNC-pincer complex to give the corresponding arylated products in high yield, wher

A simple and direct method for the palladium-catalyzed oxidative coupling of unactivated allylarenes with classic arenes

An efficient route to engineer vinylarene structures by the Pd II-catalyzed oxidative coupling of unactivated allylarenes with classic arenes was developed. The methodology features the use of unactivated allylarenes with no prefunctionalization and classic arenes without installed directing groups. A variety of vinylarenes and their saturated derivatives were obtained. They make a great couple: An efficient route to engineer vinylarene structures by PdII-catalyzed oxidative coupling of unactivated allylarenes with classic arenes is developed. The methodology features the use of unactivated allylarenes with no prefunctionalization and classic arenes without installed directing groups. A variety of vinylarenes and their saturated derivatives are obtained.

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.

Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol

An efficient synthesis of 3-aryl-1-propenyl boronates from pinacol vinyl boronic ester and allyl-substituted aromatics by cross metathesis is reported. Although the allylbenzene derivatives are prone to isomerization reaction under metathesis conditions,