104581-29-5

Upstream product

• 869808-67-3 dimethyl((4-methoxyphenyl)ethynyl)silane 
• 108-94-1 cyclohexanone 
• 768-60-5 4-methoxyphenylacetylen 
• 18275-67-7 diethyl (1-(4-methoxyphenyl)vinyl)phosphate 
• 696-62-8 para-iodoanisole 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Downstream Products

• 104581-38-6 1-[2,2-Bis-(4-methoxy-phenyl)-vinyl]-cyclohexanol 
• 104581-60-4 1-[(Z)-1,2-Bis-(4-methoxy-phenyl)-vinyl]-cyclohexanol 
• 106262-75-3 1-[(E)-2-(4-methoxyphenyl)vinyl]cyclohexanol 
• 1354640-68-8 1-((1-(2-(4-methoxyphenyl)ethynyl)cyclohexyloxy)methyl)-2-bromo-4,5-dimethoxybenzene 
• 1354640-82-6 C₂₄H₂₈O₄ 
• 1515880-70-2 8-(4-methoxyphenyl)spiro[benzo[b]pyrrolo[1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine-9,1'-cyclohexane] 
• 1515880-71-3 8-(4-methoxyphenyl)-1,3-dimethylspiro[benzo[b]pyrrolo[1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine-9,1'-cyclohexane] 
• 1334217-32-1 2-methyl-3-(4-methoxyphenyl)-1-oxaspiro[4.5]dec-2-en-4-one 
• 1007120-38-8 1‐fluoro‐2‐((4‐methoxyphenyl)ethynyl)benzene 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 1007120-37-7 2-[2-(4-methoxyphenyl)ethynyl]naphthalene 
• 123770-67-2 1-(4-((4-methoxyphenyl)ethynyl)phenyl)ethanone 
• 7380-78-1 4-(phenylethynyl)anisole 
• 913627-49-3 2-(2-(4-methoxyphenyl)ethynyl)thiophene 

Relevant academic research and scientific papers

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

It was demonstrated that the γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate as a partially bio-based solvent can be utilized as alternative reaction medium for copper- and auxiliary base-free Pd-catalyzed Sonogashira coupling reactions of aryl iodides and functionalized acetylenes under mild conditions. Twenty-two cross-coupling products were isolated with good to excellent yields (72–99%) and purity (>98%). These results represent an example which proves that biomass-derived safer solvents can be utilized efficiently in common, industrially important transformations exhibiting higher chemical and environmental efficiency.

Unusual tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes

(Chemical Equation Presented) An unusual tandem reaction sequence to form oxasilacyclopentenes from carbonyls and alkynylsilanes in the presence of a catalytic amount of nucleophilic initiator has been discovered. The reaction proceeds readily at room tem

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Tandem C-2 functionalization-intramolecular Azide-Alkyne 1,3-Dipolar Cycloaddition reaction: A convenient route to highly diversified 9H-Benzo[b]pyrrolo[1,2-g][1,2,3]triazolo[1,5-d][1,4]diazepines

An efficient diversity-oriented synthetic approach to annulated 9H-benzo[b]pyrrolo[1,2-g][1,2,3]- triazolo[1,5-d][1,4]diazepines has been developed using a Sc(OTf)3-catalyzed two-component tandem C-2 functionalization- intramolecular azide-alky

Silver-catalyzed direct addition of terminal alkynes to simple cyclic ketones in water

The first catalytic addition of terminal alkynes to simple cyclic ketones in water catalyzed by silver was developed. Cyclic ketones were reacted with terminal alkynes efficiently in water to give the corresponding propargyl alcohols. Georg Thieme Verlag

Synthesis of 2,3-diiodoindenes and their applications in construction of 13H-indeno[1,2-l]phenanthrenes

A series of 2,3-diiodoindene were synthesized at first, and 13H-indeno[1,2-l]phenanthrenes were then constructed via a Suzuki coupling reaction and subsequently a Scholl reaction. Structures of synthesized compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Their photophysical properties, such as UV-vis and FL spectra were investigated, and electronic properties were theoretically calculated by the software of Gaussian 03. The results suggested that these modified indene and indenophenanthrene compounds might have potential applications as light emitting materials.

Palladium-catalyzed intramolecular hydroarylation of 2-bromobenzyl propargyl ethers: A new access to exocyclic isochromans

An efficient, stereo- and regioselective palladium-catalyzed 6-exo-dig intramolecular hydroarylation of propargyl ethers which provides a concise access to functionalized isochromans in high yields has been developed. A wide range of substrates possessing aromatic, aliphatic and heteroaromatic alkynes can be efficiently transformed into the targeted isochromans. Irrespective of the nature of the substrates, the cyclization follows highly selective -stereo- and regiochemistry.

Perfluoro-tagged, phosphine-free palladium nanoparticles supported on silica gel: Application to alkynylation of aryl halides, Suzuki-Miyaura cross-coupling, and Heck reactions under aerobic conditions

The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd np-A/FSG) or through covalent bonding to silica gel (Pd np-B) in the alkynylation of aryl halides, in the Suzuki-Miyaura cross-coupling, as well as in the Heck reaction between methyl acrylate and aryl iodides is described. The reactions are carried out under aerobic and phosphine-free conditions with excellent to quantitative product yields in each case. The catalysts are easily recovered and reused several times without significant loss of activity. The alkynylation of aryl halides (under copper-free conditions) and the Suzuki-Miyaura cross-coupling are carried out in water. The Heck reaction of methyl acrylate with aryl iodides is best performed in MeCN. The utilization of Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported.

Copper- and phosphine-free Sonogashira coupling reaction catalyzed by polyurea-encapsulated palladium(II)

A polyurea-encapsulated palladium catalyst (Pd EnCat 30) was first applied to Sonogashira cross-coupling reactions in the absence of a copper salt co-catalyst and under phosphine-free conditions. This polymer-anchored homogeneous palladium catalyst effici

Ethynyl-cyclohexanol: an efficient acetylene surrogate in Sonogashira coupling

The Sonogashira coupling of aryl halides in the presence of 1-ethynyl-cyclohexanol as an acetylene source provides an efficient method for the synthesis of diarylacetylenes without the isolation of the appropriate arylacetylenes.