32340-38-8

Upstream product

• 124-38-9 carbon dioxide 
• 29079-00-3 4-ethynyl-1,1'-biphenyl 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 471-25-0 Propiolic acid 
• 150844-00-1 1-(biphenyl-4-yl)-2,2-dibromoethylene 
• 3218-36-8 4-Phenylbenzaldehyde 
• 5122-94-1 4-biphenylboronic acid 
• 1591-31-7 4-iodo-biphenyl 
• 1030-07-5 ethyl 3-([1,1'-biphenyl]-4-yl)propiolate 
• 88241-65-0 4-phenylcinnamic acid 
• 32244-60-3 2-[Biphenyl-4-yl-(naphthalene-2-sulfonyloxy)-methylene]-malonic acid di-tert-butyl ester 
• 32244-52-3 Di-t-butyl-p-phenylbenzoylmalonat 
• 32244-79-4 2.2-Dicarboxy-1-biphenyl-4-yl-vinylnaphthalin-β-sulfonat 

Downstream Products

• 1363436-46-7 N-[2-(4-Biphenyl-4-ylethynyl-phenyl)-1-methyl-ethyl]acetamide 
• 29079-15-0 1,4-di[(1,1′-biphenyl)-4-yl]buta-1,3-diyne 
• 36803-53-9 1-([1,1′-biphenyl]-4-yl)-2-phenylethane-1,2-dione 
• 941666-88-2 (E)-2-(2-([1,1′-biphenyl]-4-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 15784-39-1 4-(phenylethynyl)-1,1'-biphenyl 

Relevant academic research and scientific papers

Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide

The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide. The method comprises the experimental steps that alkyne, alkali and a solvent are added into a reaction tube, the alkyne serves as a raw material, the alkali and the solvent provide a strong alkaline environment, CO2 is introduced into a reaction container to form a carbon dioxide atmosphere, heating and stirring reaction are carried out, after the reaction is finished, cooling is carried out to the room temperature, extraction and liquid separation are carried out, a water layer is acidified, then separation and purification are further carried out, and the acetylenic acid compound is obtained. The method is carried out under the conditions of low temperature and normal pressure, does not need to add a metal catalyst, is single in product and convenient to separate, good in substrate applicability and safe and simple to operate, and has potential industrial application prospects and good economic benefits.

Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes

An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.

Microwave-assisted fabrication of a mixed-ligand [Cu4(μ3-OH)2]-cluster-based metal–organic framework with coordinatively unsaturated metal sites for carboxylation of terminal alkynes with carbon dioxide

The development of efficient and stable metal–organic framework (MOF) catalysts with coordinatively unsaturated metal sites for modern organic synthesis is greatly important. Herein, a robust [Cu4(μ3-OH)2]-cluster-based MOF (Cu-MOF) with a mixed-ligand system was successfully fabricated by a microwave-assisted method under mild conditions. The as-prepared Cu-MOF catalyst possessing unsaturated Cu (II) sites exhibited excellent catalytic activity toward the direct carboxylation of 1-ethynylbenzene with CO2, and various propiolic acid derivatives were synthesized in moderate to good yields under optimized reaction conditions. Furthermore, the catalyst remained stable and could be easily recycled for five sequential runs without incredible decrease in catalytic efficiency.

Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions

A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).

Visible light induced 3-position-selective addition of arylpropiolic acids with ethersviaC(sp3)-H functionalization

Although the 2-position-selective decarboxylative coupling or addition of arylpropiolic acids with cyclic ethers has been intensively investigated, selective functionalization of arylpropiolic acids at the 3-position is still a big challenge. Herein, an i

A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids

An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene tetrahydrofuran and tetrahydrofuran diene.

Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis

A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination. (Figure presented.).

NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers

A direct alkenylation of cyclic ethers via radical cross decarboxylative coupling process catalyzed by NiCl2 and using DTBP as radical initiator and oxidant was developed. A variety of arylpropiolic acids and cyclic ethers were transformed into the corresponding 2-arylvinyl cyclic ethers in moderate to excellent yields. Mechanistic experiments were conducted to determine the nature of the reaction intermediates, and a plausible reaction mechanism involving NiCl2-promoted radical process was proposed.

Rhodium(III)-catalysed cascade [3 + 2] annulation of: N -aryloxyacetamides with 3-(hetero)arylpropiolic acids: Synthesis of benzofuran-2(3 H)-ones

Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).