156423-16-4

Upstream product

• 1866-39-3 trans-p-methylcinnamic acid 
• 75-11-6 diiodomethane 
• 104-81-4 4-Methylbenzyl bromide 
• 214907-11-6 4-methylstyrenylboronic acid 
• 72316-17-7 (E)-2-(4-methylphenyl)ethenylboronic acid 
• 122-00-9 para-methylacetophenone 
• 3020-28-8 (iodomethyl)triphenylphosphonium iodide 
• 104-87-0 4-methyl-benzaldehyde 
• 1866-39-3 4-methylcinnamic acid 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 3333-13-9 p-allyltoluene 
• 766-97-2 4-n-methylphenylacetylene 
• 149777-84-4 4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane 

Downstream Products

• 33356-85-3 (E)-1-(4-tolyl)-1,3-butadiene 
• 89510-66-7 (E,E)-1-methoxy-4-[4-(4-methylphenyl)-1,3-butadienyl]benzene 
• 60466-41-3 (E)-1-(phenylselenenyl)-2-(4-methylphenyl)ethene 
• 1206884-50-5 2-(4-methylphenyl)pyrazolo[1,5-a]pyridine 
• 1233718-81-4 (E)-1-(4-methylstyryl)-4-phenyl-1H-imidazole 
• 61153-37-5 1-(1E)-1-hexen-1-yl-4-methylbenzene 
• 2077-30-7 (E)-1-methyl-4-(prop-1-enyl)benzene 
• 42079-98-1 (E)-1-methyl-4-(oct-1-en-1-yl)benzene 
• 111133-19-8 trimethyl<3-(4-methylphenyl)-2-propenyl>silane 

Relevant academic research and scientific papers

Stereoselective Synthesis of Vinyl Iodides from Vinylboronate Pinacol Esters using ICl.

Polyenyl-1-boronic acids, with hindered pinacol esters, are difficult to transform into the corresponding Z- or E-iodides under literature reaction conditions.However, reaction of trans-polyenyl-1-boronate pinacol esters with sodium methoxide, followed by

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Oxidative Addition of Alkenyl and Alkynyl Iodides to a AuI Complex

The first isolated examples of intermolecular oxidative addition of alkenyl and alkynyl iodides to AuI are reported. Using a 5,5′-difluoro-2,2′-bipyridyl ligated complex, oxidative addition of geometrically defined alkenyl iodides occurs readily, reversibly and stereospecifically to give alkenyl-AuIII complexes. Conversely, reversible alkynyl iodide oxidative addition generates bimetallic complexes containing both AuIII and AuI centers. Stoichiometric studies show that both new initiation modes can form the basis for the development of C?C bond forming cross-couplings.

Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides

An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.

Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

A convenient, highly regioselective synthesis of five-membered cyclic vinyl(aryl)iodonium salts directly from β-iodostyrenes is presented. An X-ray crystal structure confirms the identity of these heterocycles. These λ3-iodanes can be converted

A stereoselective synthesis of (E)- or (Z)-β-arylvinyl halides via a borylative coupling/halodeborylation protocol

A new stereoselective method for the synthesis of (E)-β-arylvinyl iodides and (E)- or (Z)-β-arylvinyl bromides from styrenes and vinyl boronates on the basis of a one-pot procedure via borylative coupling/halodeborylation is reported. Depending on the halogenating agent as well as the mode of the halodeborylation reaction, (E) or (Z) isomers are selectively formed.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

Ruthenium-catalyzed one-pot synthesis of (E)-(2-arylvinyl)boronates through an isomerization/cross-metathesis sequence from allyl-substituted aromatics

We described the efficient preparation of (E)-(2-arylvinyl)boronates from allylbenzene derivatives on the basis of an isomerization/cross-metathesis sequence catalyzed by a modified Hoveyda-Grubbs catalyst. The implementation of the experimental procedure was simple and compatible with a large variety of substrates. This methodology provides a new chemical transformation not described to date. Allyl-substituted aromatics can thus be converted into diversely functionalized compounds, such as (E)-stilbene derivatives or (E)-vinyl azides, in only two steps. Copyright

Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes

Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

Copper oxide nanoparticles catalyzed vinylation of imidazoles with vinyl halides under ligand-free conditions

Recyclable copper oxide nanoparticles catalyzed most efficient and straightforward protocol for the vinylation of imidazoles with vinyl halides under ligand-free conditions. Utilizing this protocol various imidazoles were cross-coupled with different substituted vinyl halides to get the corresponding products in excellent yields with the retention configuration.