70127-39-8

Upstream product

• 591-50-4 iodobenzene 
• 4302-52-7 4-ethynylveratrole 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 536-74-3 phenylacetylene 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 13146-23-1 copper(I) phenylacetylenide 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 2859-78-1 4-Bromoveratrole 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 603-33-8 triphenylbismuthane 
• 118199-01-2 2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene 

Downstream Products

• 3892-92-0 (E)-3,4-dimethoxystilbene 
• 169120-65-4 N-(3,4-dimethoxyphenyl)-2-phenylacetamide 
• 79997-18-5 1-(3,4-dimethoxyphenyl)-2-phenylethane-1,2-dione 

Relevant academic research and scientific papers

Hybrid hydrogels loaded with palladium nanoparticles – Catalysts for environmentally-friendly Sonogashira and Heck cross-coupling reactions

Palladium nanoparticles (PdNPs) were encapsulated within hybrid hydrogels made from an acylhydrazide-functionalised 1,3:2,4-dibenzylidene sorbitol (DBS-CONHNH2) low-molecular-weight gelator (LMWG) combined with agarose polymer gelator via in situ reduction of Pd(II). These heterogeneous gel-phase catalysts were successfully applied for copper-, amine- and phosphine-free Sonogashira cross-coupling reactions under environmentally-friendly conditions without the need for inert atmosphere reaction conditions. The PdNP-loaded gel was reused in Sonogashira couplings up to at least five times with no adverse effect on yield. The performance of solvated PdNP-loaded gel catalysts was compared with the dried xerogels. The xerogels can be used at higher temperatures, enhancing reaction kinetics albeit lowering reaction selectivity, but unlike the solvated gels, were unable to be easily recycled and reused. The PdNP-loaded gels also had good activity in Heck reactions, and although longer reaction times or higher temperatures were required than for the Sonogashira reaction, the reaction conditions were mild for a Heck coupling. In summary, we demonstrate a ‘waste-to-wealth’ methodology in which Pd(II) ‘waste’ is converted into a valuable gel-phase catalyst that can be used for green Sonogashira and Heck cross-coupling reactions.

E- and Z-Selective Transfer Semihydrogenation of Alkynes Catalyzed by Standard Ruthenium Olefin Metathesis Catalysts

Selective transfer semihydrogenation of alkynes to yield alkenes was achieved with commercial first and second generation Hoveyda-Grubbs catalysts and formic acid as a hydrogen donor. This catalytic system is distinguished by its selectivity and compatibility with many functional groups (halogens, cyano, nitro, sulfide, alkenes). The metathetic activity of the ruthenium catalysts may be utilized in tandem sequences of olefin metathesis plus alkyne reduction.

Supramolecular ensemble of a TICT-AIEE active pyrazine derivative and CuO NPs: A potential photocatalytic system for sonogashira couplings

The donor-acceptor system 4 having pyrazine scaffold as an acceptor moiety coupled to donor amino groups through rotatable phenyl rings has been synthesized, which formed aggregates in aqueous media, exhibited copper induced restriction to intramolecular rotation, and served as a "not quenched" probe for the detection of copper(II) ions. During this process, the aggregates of derivative 4 acted as reactors and stabilizers for the generation of CuO NPs and themselves became oxidized to form polyamine derivative 6. Interestingly, the oxidized species 6 in combination with copper oxide nanoparticles served as light-harvesting antennas and exhibited excellent photocatalytic efficiency in Sonogashira coupling under mild and eco-friendly conditions (room temperature, aqueous media, aerial conditions, and visible light irradiation).

Palladium-Catalyzed Domino Process: Synthesis of Symmetrical Diarylalkynes, cis- and trans-Alkenes using Lithium Acetylide as a Synthon

An efficient domino protocol has been developed for the synthesis of symmetrical diarylalkynes. Notably, the method was successful in the presence of a palladium catalyst without the support of a copper co-catalyst. Significantly, the method enabled the use of the commercially available and cheap lithium acetylide ethylenediamine complex as a source of acetylene for the construction of dual C-C bonds, with a wide range of compatibility towards various substituents of the aryl bromides/iodides. Significantly, this protocol was successfully applied to the synthesis of cis- and trans-alkenes in a highly stereoselective manner in a sequential one-pot process.

Expanding the oxidative chemistry of organocopper reagents: Facile oxidative cross-coupling of copper acetylides with arylboronic acids

We have developed an efficient procedure for oxidative cross-coupling between arylboronic acids and alkynylcopper reagents. Upon simple addition of 1,10-phenanthroline in the presence of oxygen, these highly stable, readily available polymeric reagents are easily activated and transfer their alkynyl group after subsequent transmetallation with the boronic acid. These results further expand the oxidative chemistry of organocopper compounds together with providing a user-friendly entry to diaryl acetylenes.

Hexaphenylbenzene-based polymers of intrinsic microporosity

Microporous polymers derived from the 1,2- and 1,4-regioisomers of di(3′,4′-dihydroxyphenyl)tetraphenylbenzene have very different properties with the former being composed predominantly of cyclic oligomers whereas the latter is of high molar mass suitable for the formation of robust solvent-cast films of high gas permeability.

A general palladium-catalyzed sonogashira coupling of aryl and heteroaryl tosylates

Coupled up: A new general palladium-catalyzed procedure for the cross-coupling of aryl and heteroaryl tosylates is described. This highly versatile and efficient process can be used for the synthesis of a wide variety of functionalized alkynes (see scheme).

Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles

Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.

Synthesis substituent interactions of tricarbonylchromium-complexed arylalkynylbenzenes - novel organometallic push-pull chromophores

The tricarbonylchromium complexes chlorobenzene 1 reacts with terminal alkynes 2 through a palladium-copper-catalyzed coupling to give a variety of Cr(CO)3-complexed phenylethynyl arenes, heteroarenes and ferrocene 3 in good to excellent yield.

Oxidation of Aromatic Compounds. IV. Oxidation of Symmetrical Diarylacetylenes in the CF3COOH-CH2Cl2-PbO2 System. A New One-Pot Synthesis of 1,2,3,4-Tetraaryl-2-butene-1,4-diones

Oxidation of symmetrical diarylacetylenes in the CF3COOH-CH2Cl2-PbO2 system (0-20 deg C, 1-3 h) yields 1,2,3,4-tetraaryl-2-butene-1,4-diones.According to (1)H NMR and GC-MS data the compounds synthesized have Z configuration.