1104996-91-9

Upstream product

• 106-43-4 para-chlorotoluene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 5720-05-8 4-methylphenylboronic acid 
• 157339-09-8 carbonic acid methyl ester 1-phenyl-but-3-enyl ester 
• 100-52-7 benzaldehyde 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 159755-12-1 1-(1-bromoethyl)-4-methylbenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 60672-33-5 4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 63537-05-3 (E)-(3-chlorobut-1-en-1-yl)benzene 
• 100-42-5 styrene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 

Relevant academic research and scientific papers

Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols

Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds readily under mild conditions in the presence of zinc powder and MgCl2to produce allylarenes in 25-92% yields. The reaction shows high regioselectivit

Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides

An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,

Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.

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.

Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles

We herein report a transition-metal-free cross-coupling between secondary alkyl halides/mesylates and aryl/alkenylboronic acid, providing expedited access to a series of nonchiral/chiral coupling products in moderate to good yields. Stereospecific SN2-type coupling is developed for the first time with alkenylboronic acids as pure nucleophiles, offering an attractive alternative to the stereospecific transition-metal-catalyzed C(sp2)-C(sp3) cross-coupling.

Olefination of carbonyl compounds through reductive coupling of alkenylboronic acids and tosylhydrazones

The partners decide: The C-C bond-forming reductive cross-coupling of alkenylboronic acids and tosylhydrazones takes place under mild reaction conditions without the need of a metal catalyst, thus giving rise to olefination-type products (see scheme). The position of the double bond in the product is determined by the structure of the coupling partners. Copyright

Rhodium-catalyzed allylic substitution reactions with indium(III) organometallics

A novel rhodium-catalyzed allylic substitution reaction using indium organometallics is reported. Aryl- and heteroarylindium reagents reacted in THF at 80 °C with primary and secondary allyl halides and their derivatives under rhodium(I) catalysis to afford the α-substituted products in good yields and with high regio- and stereoselectivity. The reaction takes place with substoichiometric amounts of the triorganoindium reagents, which demonstrates the efficiency of the indium-rhodium transmetallation process in carbon-carbon bond-forming reactions. Copyright

Iron-catalyzed stereospecific olefin synthesis by direct coupling of alcohols and alkenes with alcohols

Chemical equations presented. An efficient Fe(III)-catalyzed direct coupling of alkenes with alcohols and cross-coupling of alcohols with alcohols to give the corresponding substituted (E)-alkenes stereospecifically is demonstrated. Additionally, this reaction could be scaled up. The kinetic isotope effect (KIE) experiments indicated a typical secondary isotope effect in this process. Although benzylic alcohols were effective substrates, mild conditions, atom efficiency, environmental soundness, and stereospecificity are features that make this procedure very attractive.

Direct coupling of alcohols with alkenylsilanes catalyzed by indium trichloride or bismuth tribromide

Indium halides or bismuth halides catalyzed the coupling of various alcohols with alkenylsilanes to give the corresponding alkenes stereospecifically without any other activators. The Royal Society of Chemistry 2008.