1266357-81-6

Upstream product

• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 1066-54-2 trimethylsilylacetylene 
• 77295-62-6 1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 212138-65-3 2,4-dichloro-1-(2,2-dibromovinyl)benzene 
• 114943-73-6 2-(4-Benzyloxyphenyl)-1,1-dibromoethylene 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 1082769-34-3 2-bromo-5-methoxy-benzo[b]thiophene 

Relevant academic research and scientific papers

Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU?H2O

An efficient synthesis of 1,3-diynes directly from 1,1-dibromoalkenes has been achieved by utilizing hydrated 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU.H2O) as a sole reagent and a catalyst CuI. In general, 1,3-diynes were synthesized from corresponding terminal alkynes, which in turn were obtained from 1,1-dibromoalkenes. The DBU.H2O allowed the synthesis of 1,3-diynes not only in a pot-efficient manner but also under solvent-free conditions at ambient temperature. A plausible mechanism is proposed via 1-bromoalkynes intermediate instead of terminal alkynes.

Organic transformations catalyzed by palladium nanoparticles on carbon nanomaterials

Abstract: An efficient C–C bond coupling reactions (Suzuki–Miyaura and Glaser) catalyzed by PdO/GO nano-catalyst is presented. In addition, PdO/MWCNT nano-catalyst-mediated domino one-pot synthesis of 2-alkyl/2-aryl benzofurans has been accomplished from 2-iodophenols and terminal alkynes. The formation of benzofurans proceeds through intermolecular Sonogashira reaction followed by intramolecular nucleophilic addition of internal hydroxyl group onto the acetylenic bond. The catalyst PdO/GO has been reused successfully, with nearly no loss of activity up to 5 cycles. Graphical Abstract: : Synopsis: An efficient PdO/GO and PdO/MWCNT nanocatalysts have been developed for C–C coupling reactions like Suzuki and Glaser coupling reactions, multi-catalytic one-pot synthesis of 2-aryl, 2-alkyl benzofurans staring from 2-iodophenols and terminal alkynes. The protocol involves formation of benzofuran derivatives, i.e., Sonogashira reaction followed by 2-ethynyl phenol cyclization. [Figure not available: see fulltext.]

[Cu]-catalyzed direct coupling of dibromoalkenes: Synthesis of symmetrical 1,3-diynes and triazoles

An efficient [Cu]-catalyzed homocoupling of 1,1-dibromoalk-1-enes is described for the synthesis of symmetrical 1,3-diyines. The method showed good substrate scope and amenable to aryl and heteroaryl systems. Significantly, the strategy was also successfully applied to the sequential one-pot synthesis of triazoles.

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence

2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira-Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations.

Copper immobilized on nano-silica triazine dendrimer (Cu(ii)-TD@nSiO 2) catalyzed synthesis of symmetrical and unsymmetrical 1,3-diynes under aerobic conditions at ambient temperature

A highly efficient route for the synthesis of symmetrical and unsymmetrical 1,3-diynes has been developed by Cu(ii)-TD@nSiO2/DBU catalyzed homocoupling/heterocoupling of aromatic as well as aliphatic terminal alkynes under aerobic conditions at ambient temperature. The catalyst could be easily recovered and reused several times without significant loss of its activity.

Domino synthesis of 1,3-diynes from 1,1-dibromoalkenes: A Pd-catalyzed copper-free coupling method

Pd-catalyzed domino synthesis of 1,3-diynes was accomplished using 1,1-dibomoalkenes under copper-free coupling conditions. This domino procedure involves base mediated in situ generation of 1-bromoalkyne and its subsequent coupling to give 1,3-diyne. The optimized copper-free coupling method afforded good to high yields of symmetrical 1,3-diynes in a one-pot operation.

Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: A comparative study of several methods

Several methods for the preparation of (Z) trimethoxystyrene derivatives 1 were investigated. After finding that the Wittig reaction led to unsatisfactory results, three different strategies were considered: a Suzuki coupling with a stereodefined monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends on the target compound but the semi-hydrogenation, which avoids the use of a toxic tin reducing agent, should be generally preferred.

Consecutive one-pot sonogashira-glaser coupling sequence- Direct preparation of symmetrical diynes by sequential Pd/Cu catalysis

Sonogashira coupling and the catalytic Glaser coupling are both catalyzed by the Pd-Cu complex couple and can be concatenated to a consecutive sequentially Pd/Cu-catalyzed process in a one-pot fashion, and air oxygen serves as the only oxidant in the second step. In a pseudo-four-component synthesis, a broad variety of symmetrically substituted 1,4-bis(hetero)aryl-1,3-butadiynes are obtained in good to excellent yields. Interestingly, the presence of iodide ions has been found to be advantageous over other halides to trigger the Pd/Cu-catalyzed Glaser step, and Pd and Cu species, as well as triethylamine as a base, are prerequisite for both couplings, which proceed with higher efficiency if performed in a one-pot sequence. Two catalytic alkyne coupling reactions were combined in a consecutive sequentially Pd/Cu-catalyzed process to furnish a novel pseudo-four-component synthesis of a variety of symmetrically substituted 1,4-bis(hetero)aryl-1,3-butadiynes in goodyields. Pd and Cu species and triethylamine (base) are essential for the couplings, which proceed with higher efficiency if performed in a one-pot sequence. Copyright