16664-50-9

Upstream product

• 1483-82-5 phenylethynyl chloride 
• 17049-49-9 octylmagnesium bromide 
• 140472-48-6 1,1-dibromo-2-phenyldec-1-ene 
• 629-27-6 1-Iodooctane 
• 536-74-3 phenylacetylene 
• 764-93-2 1-decyne 
• 108-86-1 bromobenzene 
• 3757-88-8 tributylstannylethynylbenzene 
• 108-90-7 chlorobenzene 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 131379-13-0 octylzinc(II) bromide 
• 111-83-1 1-bromo-octane 
• 4440-01-1 lithium phenylacetylide 
• 16664-48-5 6-bromo-1-phenyl-1-hexyne 

Downstream Products

• 62839-72-9 (Z)-1-(dec-1-enyl)benzene 
• 110792-92-2 (Z)-(dec-3-en-1-ynyl)benzene 

Relevant academic research and scientific papers

Sonogashira Coupling Reaction with Palladium Powder, Potassium Fluoride in Aqueous Media

A Sonogashira coupling reaction of aromatic iodides and bromides with terminal alkynes in the presence of palladium powder, potassium fluoride, cuprous iodide, and triphenylphosphine in aqueous media was developed. The reaction generates the corresponding

EIN EINFACHES VERFAHREN ZUR ALKYLIERUNG VON ARYLALKINEN

Arylalkynes are alkylated in a rapid reaction and under mild conditions by alkyl iodides in the presence of powdered KOH and 18-crown-6

Nickel-catalyzed direct alkylation of terminal alkynes at room temperature: A hemilabile pincer ligand enhances catalytic activity

Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there h

Nickel-Catalyzed Sonogashira Coupling Reactions of Nonactivated Alkyl Chlorides under Mild Conditions

The two nickel chlorides1and2with [P,S] and [P,Se] bidentate ligands, respectively, were synthesized and used as catalysts for Sonogashira coupling reaction. Both1and2are efficient catalysts for Sonogashira C(sp3)-C(sp) coupling reactions. Comp

Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes

Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.

Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes

C(carbene)N(amido)N(amine)-pincer nickel(ii) complexes [iPrCNN-Ni-Br] (6), [nBuCNN-Ni-Br] (7) and [BnCNN-Ni-Cl] (8) were synthesized. The catalytic performance of complexes 6-8 for Sonogashira cross-coupling reactions was

Cross-coupling reactions using porous multipod Cu2O microcrystals as recoverable catalyst in aqueous media

Porous multipod Cu2O microcrystals were found to be an efficient, highly recyclable and eco-friendly catalyst for the cross-coupling reactions of aryl halides and terminal alkynes with high yields in aqueous media. Noteworthy, the Cu2O catalyst can be reused for several times without significant decrease in catalytic activity.

Gallic acid-derived palladium(0) nanoparticles as in situ-formed catalyst for Sonogashira cross-coupling reaction in ethanol under open air

A simple and eco-friendly protocol using gallic acid-derived palladium(0) nanoparticles as in situ-formed catalyst for Sonogashira reactions in ethanol under optimum thermal conditions have been developed. Excellent yields were obtained with the addition of a small amount of gallic acid (1 mol%) to the reaction mixture. The formation of the PdNPs was confirmed by using UV/Vis spectroscopy, and their size and morphology were determined by TEM and XRD analysis. Both aliphatic and aromatic terminal alkynes displayed efficient reactivity with the catalytic system. Moreover, the reaction condition is highly compatible with less reactive aryl bromides at moderate temperature, and further can be reused repeatedly up to four cycles. Since gallic acid is a non-toxic naturally abundant phytochemical, the present method provides an efficient alternative route for Sonogashira reaction with natural feedstock as additive.

In situ generation of palladium nanoparticles using agro waste and their use as catalyst for copper-, amine- and ligand-free Sonogashira reaction

The use of water extract of waste papaya bark ash for the in situ generation of palladium nanoparticles (Pd NPs) as an efficient and environmentally friendly basic medium for the Sonogashira reaction at room temperature is reported. This methodology follows green chemistry principles as the reaction is performed using agro waste (natural feedstock) for the generation of the Pd NPs as well as for providing a basic medium for the reaction in the absence of any additional organic or inorganic base, ligand and copper salt, giving excellent yield of cross-coupled product at room temperature. The reaction conditions are compatible with electronically diverse aryl iodides and electronically diverse alkyne derivatives.

N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates

(NHC)-Cu-catalyzed C(sp)-C(sp3) bond formation has been successfully achieved under mild conditions. Nonactivated alkyl triflates, which could be easily derived from alcohols, were utilized as C-O electrophiles. Mechanistic studies suggested th