111887-18-4

Upstream product

• 696-62-8 para-iodoanisole 
• 2028-63-9 but-3-yn-2-ol 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 75-07-0 acetaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 103253-60-7 4-trimethylsilyl-3-butyn-2-ol 
• 64-17-5 ethanol 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 768-60-5 4-methoxyphenylacetylen 
• 123-11-5 4-methoxy-benzaldehyde 
• 81532-80-1 4-(4-methoxyphenyl)-3-butyn-2-one 

Downstream Products

• 1186524-47-9 4-(1-methoxy-pentylidene)-3-(4-methoxy-phenyl)-5-methyl-3-dihydro-furan-2-one 
• 1188375-80-5 4-iodo-4-(p-methoxyphenyl)-3-(n-pentyl)-3(Z)-buten-2-ol 
• 102821-81-8 (E)-1-(4-methoxyphenyl)-2-phenyl-2-buten-1-one 
• 1450831-20-5 2-chloro-4-(4-methoxyphenyl)but-3-yne 
• 1450831-24-9 C₁₂H₁₁F₃O 
• 1131-79-9 1-(4-methoxy-phenyl)-but-2-en-1-one 
• 1443527-03-4 (S)-1-(4-methoxyphenyl)-3-(p-tolyl)butan-1-one 
• 1109280-52-5 1-(4-methoxyphenyl)-3-(p-tolyl)butan-1-one 
• 1393376-12-9 C₂₂H₂₂O₂ 
• 180691-76-3 1-(buta-1,2-dien-1-yl)-4-methoxybenzene 
• 1380423-64-2 (E)-benzyl 4-(4-methoxyphenyl)but-3-en-2-ylcarbamate 
• 81532-80-1 4-(4-methoxyphenyl)-3-butyn-2-one 
• 1334158-44-9 (Z)-4-(4-methoxyphenyl)-3-phenylbut-3-en-2-ol 
• 76217-07-7 4-(4-methoxyphenyl)-4-phenylbutan-2-one 

Relevant academic research and scientific papers

A highly effective Pd/Cu-catalyzed coupling reaction of terminal alkynes with organic halides promoted by tetrabutylammonium fluoride or hydroxide

Coupling reaction of terminal alkynes catalyzed by Pd/Cu with several organic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide (TBAOH) as an activator. Treatment of 1-octyne and 4-methoxy-iodob

A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes

Visible-light-promoted intermolecular radical cyclization of disulfides and alkynes has been developed. Benzothiophenes bearing ester, ketone, aldehyde and aryl substituents were synthesized in good yields. The reaction was carried out in the absence of t

Integrating Reactors and Catalysts through Three-Dimensional Printing: Efficiency and Reusability of an Impregnated Palladium on Silica Monolith in Sonogashira and Suzuki Reactions

For this work, an integrated system composed of a polypropylene reactor and a palladium on silica monolithic catalyst was designed and manufactured by 3D-printing. These devices are able to perform solution phase chemistry in a robotic orbital shaker. The capped reactor was obtained in its entirety by 3D-printing, using polypropylene and fused deposition modeling. The monolithic catalyst was also obtained by 3D-printing -robocasting- of a silica support, sintering and subsequent palladium deposition through the wet impregnation method. The catalytic efficiency in Sonogashira or Suzuki reactions as well as the recyclability of the entire system – catalyst+reactor – were studied. The strong electrostatic adsorption (SEA) of the palladium on sintered silica and the reduced mechanical stress produced by the convenient adjustment of the catalyst into the polypropylene reactor makes the catalytic system reusable without significant loss of catalytic activity.

Green synthesis of water-dispersable palladium nanoparticles and their catalytic application in the ligand- and copper-free Sonogashira coupling reaction under aerobic conditions

Pd nanoparticles were prepared from PdCl2 by green method and were characterized with UV-vis, XRD and TEM methods. Catalytic studies indicated that Pd nanoparticles exhibited high activity for ligand-, amine- and copper-free Sonogashira couplin

Palladium nanoparticles immobilized on chemically modified silica gel: Efficient heterogeneous catalyst for suzuki, stille and sonogashira cross-coupling reactions

Nanoparticulate palladium (Pdnp-2) supported on polyethylene glycol-functionalized silica gel is an excellent heterogeneous catalytic system for Suzuki, Sonogashira and Stille cross-coupling reactions that afford products in high yield. The immobilized palladium nanoparticles were readily prepared by reaction of modified silica gel (1) with potassium tetrachloropalladate(II) in the presence of an acyl metal salt of a Fischer carbene complex. The nanoparticles were characterized by X-ray diffraction (XRD) and transmission electron microscopy (TEM). The catalyst (Pdnp-2) is thermally stable, insensitive to oxygen, and recyclable. The catalyst has been used for five cycles without noticeable loss of catalytic activity. Copyright

Synthesis of Alkylidene(gem-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland-Claisen Rearrangement Sequence

A one-pot difluorocyclopropenation/Ireland-Claisen rearrangement sequence applied to readily available propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of the unstable 3,3-difluorocyclopropenylcarbinyl glycolates arising from the difluorocyclopropenation. The Ireland-Claisen rearrangement proceeds with high diastereoselectivity and chirality transfer to afford alkylidene(gem-difluorocyclopropanes) incorporating a quaternary stereocenter and a protected glycolic acid moiety, which are useful building blocks for the preparation of functionalized gem-difluorocyclopropanes.

Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols

An efficient base catalyzed oxacyclization of Z-enynols has been developed under transition metal-free reaction conditions, thus resulting in a variety of new di-, tri-, and tetra-substituted furans. This approach allowed us to obtain 32 new compounds. Furthermore, DFT calculations were realized to depict a relationship between the natural population analysis and experimental results with alkyl or aryl groups for the synthesis of 2-benzylfuran. A one-pot Sonogashira/oxacyclization approach offers a flexible, robust and efficient alternative to base catalyzed cyclization is also carried out.

An efficient nanocluster catalyst for Sonogashira reaction

Pd together with CuI has been well known as the catalyst towards Sonogashira reaction, which provides an effective route to functional alkynes. However, the achievement of high activity and selectivity of this catalytic system is still challenging in some cases. Illustrative examples include their low activity for aryl chloride substrates, and switched selectivity to oxidative coupling products in air atmosphere. In this work, a Cu-incorporated Au13 nanocluster [Au13Cu2(PPh3)6(SC2H4Ph)6]+[NO3]- (Au13Cu2) was designed and prepared in high yield via rapid synthesis. This atomically precise nanocluster shows the potential to be a novel catalytic system for Sonogashira reaction, featuring high activity and selectivity, as well as good recyclability even in air atmosphere.

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).

Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes

An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.