33560-74-6

Upstream product

• 89343-06-6 tris-iso-propylsilyl acetylene 
• 90585-32-3 1,1-dibromo-2-(2-methoxyphenyl)ethene 
• 536-74-3 phenylacetylene 
• 50-00-0 formaldehyd 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 108-18-9 diisopropylamine 
• 529-28-2 4-iodoanisol 
• 471-25-0 Propiolic acid 
• 1104630-92-3 methyl 3-bromothieno[3,2-b]pyridine-2-carboxylate 
• 135-02-4 ortho-anisaldehyde 
• 1208500-32-6 1-(2-iodoethynyl)-2-methoxybenzene 
• 578-57-4 2-bromoanisole 
• 40904-92-5 4-(2'-methoxyphenyl)-2-methyl-3-butyn-2-ol 
• 7342-00-9 3-(2-methoxyphenyl)prop-2-ynoic acid 

Downstream Products

• 1448422-11-4 1-(2-methoxyphenyl)-1,3-octadiyne 

Relevant academic research and scientific papers

Method for preparing conjugated diyne compound by using copper complex

The invention relates to a method for preparing a conjugated diyne compound by using a copper complex. The method comprises the following step of: in the presence of alkali, carrying out a Glaser coupling reaction at room temperature by using alkyne as a raw material, the copper complex containing ortho-carborane Schiff base ligand as a catalyst and air as an oxidizing agent to prepare the conjugated diyne compound. Compared with the prior art, the copper complex containing the ortho-carborane Schiff base ligand is used for efficiently catalyzing the Glaser coupling reaction of alkyne to prepare the conjugated diyne compound; and the method has the advantages that selectivity is good, a catalyst dosage is low, reaction conditions are mild, a reaction can be performed in an open manner (wherein air is used as an oxidizing agent), a reaction rate is high, yield is relatively high, a substrate range is wide, and the method has wide application prospects in industry.

Synthesis of benzo[b]chalcogenophenes fused to selenophenesviaintramolecular electrophilic cyclization of 1,3-diynes

We describe herein an alternative and transition-metal-free procedure for the access of benzo[b]chalcogenophenes fused to selenophenesviaintramolecular cyclization of 1,3-diynes. This efficient protocol involves a double cyclization of 1,3-diynyl chalcogen derivatives promoted by the electrophilic species of organoselenium generatedin situby the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone in acetonitrile as solvent in an open-flask at 80 °C. In this study, 15 selenophenes with broad substrate scope were prepared in moderate to excellent yields (55-98%) with short reaction times (0.5-3.0 h).

Divergent Carbocatalytic Routes in Oxidative Coupling of Benzofused Heteroaryl Dimers: A Mechanistic Update

Mildly thermal air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’-dimers, e.g., 2-(benzofuran-2-yl)-1H-indole, to chiral 3,3’-coupled cyclooctatetraenes or carbazole-type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl-type arenium cation mechanisms lead to different products with 2-(benzofuran-2-yl)-1H-indole, being in accord with experimental product distributions.

Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through in Situ Reduction of Elemental Selenium in Superbasic Media

A series of new 2,5-disubstituted selenophene derivatives are described from elemental selenium and 1,3-diynes in superbasic media. The activation of elemental selenium in a KOH/DMSO system allows cyclization with conjugated diynes at room temperature. The cyclization reaction is extended to a broad range of functional groups, for which photophysics were experimentally and theoretically investigated. The selenophene derivatives present absorption maxima in the UV-A region and fluorescence emission in the violet-to-blue region. Fluorescence decay profiles were obtained showing a monoexponential decay with fast fluorescence lifetimes (～0.118 ns), as predicted by the Strickler-Berg relations. In general, in both investigations, no dependence on the solvent polarity on the absorption and emission maxima location was observed. On the other hand, solvents and substituents are shown to play a role in the fluorescence quantum yield values. In addition, a fluorescence self-quenching behavior could be observed, related to a photoinduced electron-transfer mechanism. Theoretical calculations performed at the MP2/ADC(2)/cc-pVDZ level of theory were performed in order to investigate the photophysical features of this series of selenophene derivatives.

Transition-metal-free variant of Glaser- and Cadiot-Chodkiewicz-type Coupling: Benign access to diverse 1,3-diynes and related molecules

Efficient and transition-metal-free transformations towards the synthesis of 1,3-diynes have been described from their corresponding terminal acetylenes or 1,1-dibromo-1-alkenes. The efficiency of molecular iodine as catalyst in aqueous medium, driven the transformation to afford 1,3-diynes in moderate to good yields. The developed reaction conditions revealed appreciable functional group tolerance in aqueous medium. Further, the scope of the transition-metal-free approach for the synthesis of 1,3-enynes has been investigated using terminal alkynes as easy available precursors.

Ligand and additive free aerobic synthesis of diynes using Pd-CuFe2O4magnetic nanoparticles as an efficient reusable catalyst

Herein, we present the synthesis of Pd-CuFe2O4 magnetic nanoparticles as an efficient and recyclable catalyst for the oxidative homocoupling of various terminal alkynes to form symmetric 1,3-diynes. The catalyst was found to be effective with very low palladium loading. The protocol has the advantages of easy synthesis of the catalyst, mild reaction conditions, short reaction times, excellent product yields and enhanced recyclability of the catalyst.

Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[ b]thiophenes

The trithiocarbonate anion (CS32-) was generated in situ from CS2 and KOH in dimethyl sulfoxide by a simple method and used as a novel synthetic equivalent of the S2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. Additionally, this system was employed for the metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes. These compounds were obtained from a cheap and readily available sulfur source in moderate to good yields, with good functional group tolerance.

Chemoselective Cobalt(I)-Catalyzed Cyclotrimerization of (Un)Symmetrical 1,3-Butadiynes for the Synthesis of 1,2,4-Regioisomers

The cobalt(I)-catalyzed cyclotrimerization of (un)symmetrical 1,4-disubstituted 1,3-butadiynes is presented. In the case of unsymmetrical 1,3-butadiynes, this reaction can generate eight 1,2,4-substituted and four 1,3,5-substituted isomers. A single 1,2,4-substituted isomer was formed in excellent yields (up to 99%) and exclusive regioselectivities (>99:1) when symmetrical or a 1,3-butadiyne with an aryl or alkyl substituent and a trimethylsilyl group were applied. A large number of products accepting a wide variety of functional groups were synthesized.

Self-assembly of catalytically active supramolecular coordination compounds within metal?organic frameworks

Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal?organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs@MOF) and its post-assembly metalation to give a PdII?AuIII supramolecular assembly, crystallography underpinned. These SCCs@MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.

Self-Assembly of Catalytically Active Supramolecular Coordination Compounds within Metal-Organic Frameworks

Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal-organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs?MOF) and its post-assembly metalation to give a PdII-AuIII supramolecular assembly, crystallography underpinned. These SCCs?MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.