168006-99-3

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 154230-29-2 (E)-4-chlorostyrylboronic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 223919-54-8 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 99-91-2 para-chloroacetophenone 
• 1615-02-7 p-chlorocinnamic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 74-88-4 methyl iodide 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 88691-45-6 (E)-[2-(4-chlorophenyl)ethenyl]trimethylsilane 

Downstream Products

• 1657-50-7 (E)-1-(4-chlorophenyl)-2-phenylethene 
• 1233718-77-8 (E)-1-(4-chlorostyryl)-4-phenyl-1H-imidazole 
• 127843-71-4 1-chloro-4-((1E,3E)-penta-1,3-dien-1-yl)benzene 
• 28446-72-2 (2E)-3-(4-chlorophenyl)acrylonitrile 
• 18684-97-4 (E)-1-(2-chlorovinyl)-4-chlorobenzene 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 33356-84-2 (E)-1-(buta-1,3-dien-1-yl)-4-chlorobenzene 
• 1258003-46-1 2-[(E)-2-(4-chlorophenyl)ethenyl]naphthalene 

Relevant academic research and scientific papers

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.

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.

Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling: Expedient construction of 2-(styrylthio)phenols

Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.

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.

New one-pot synthesis of (E)-β-aryl vinyl halides from styrenes

A new, efficient protocol for the highly stereoselective one-pot synthesis of (E)-β-aryl vinyl iodides and (￡)-β-aryl vinyl bromides from styrenes based on sequential ruthenium-catalyzed silylative coupling-N-halosuccinimide-mediated halodesilylation reactions is reported.

An efficient palladium-catalyzed Negishi cross-coupling reaction with arylvinyl iodides: facile regioselective synthesis of E-stilbenes and their analogues

A general synthetic route for the Pd-catalyzed cross-coupling of an arylzinc reagent with arylvinyl iodides (Negishi cross-coupling) has been developed. The system permits efficient and selective preparation of E-stilbenes and their analogues. It also functions effectively at low levels of catalyst loading without the need for an additional ligand and tolerates a wide range of functional groups including heteroaromatic substrates. A systematic study of various parameters was performed and correlated with catalyst-substrate activity.

Iodination of organotrifluoroborates: Synthesis of vinyl and alkynyl iodides

Vinyl- and alkynyltrifluoroborates are rapidly converted to vinyl and alkynyl iodides under mild conditions using sodium iodide in the presence of chloramine-T. The reaction is stereospecific and proceeds in excellent yield.

A facile regio- and stereocontrolled synthesis of (E)-vinylphosphonates via cross coupling of (E)-vinyl iodides with dialkyl phosphites

(E)-Vinylphosphonates were conveniently obtained under mild condition via the cross coupling of the corresponding (E)-vinyl iodides, which were obtained from the reaction of vinylzirconocenes with iodine, with dialkyl phosphites.