39672-21-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 189099-55-6 diphenyl chloro(4-chlorophenyl)methylphosphonate 
• 696-62-8 para-iodoanisole 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 873-73-4 4-n-chlorophenylacetylene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 5575-51-9 tris(4-chlorophenyl)bismuthane 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 106-39-8 bromochlorobenzene 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 1620230-46-7 6-(4-chlorophenyl)-9,11-dimethoxy-11-phenyl-11H-benzo[a]fluorene 
• 54945-17-4 1-(4-chlorophenyl)-2-(4-methoxyphenyl)-ethane-1,2-dione 

Relevant academic research and scientific papers

Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction

Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es

Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Role of substituents present in bidentate ligand frame of Cu(I) catalysts on Sonogashira cross coupling reactions

Cu(I) catalysts {[Cu(L1?4)Cl(PPh3)] where L1?4 = condensed product of 2-(1-phenylhydrazinyl)-pyridine with different benzaldehydes} were synthesized and characterized by 1H NMR, 31P NMR, UV–Vis and IR techniques. Complex 2 structure was authenticated by single crystal X-ray method. Different electron donating and withdrawing substituents are present in the ligand frame of Cu(I) catalysts and their role on Sonogashira reaction was investigated. The efficiency order of catalysts for the coupling reaction was found to be 2 > 1>3 > 4, clearly indicated the role of substituents present in the ligand frame was useful to effectively catalyze the Sonogashira reaction. The products were characterized using 1H NMR and 13C NMR.

A carrier-free and recyclable protocol for the cross-coupling of terminal alkynes with arylboronic acids in H2O/TBAB

A new and recyclable protocol was developed for Pd(OAc)2-catalyzed the cross-coupling reaction of terminal alkynes with arylboronic acids using environmentally friendly H2O/TBAB as reaction medium. A series of cross-coupling products containing internal acetylenic bond can be obtained with good selectivity and yield. The Pd(OAc)2/H2O/TBAB system was stable in the Sonogashira-type cross-coupling reaction and could be used at least three cycles without considerable decrease in catalytic performance. The results suggest that the unsupported and recyclable systems can be extended to the other realm of C&C bond formation in synthetic organic chemistry.

LiHMDS-Promoted Palladium-Catalyzed Sonogashira Cross-Coupling of Aryl Fluorides with Terminal Alkynes

A highly efficient Pd-catalyzed Sonogashira coupling of various aryl fluorides with terminal alkynes in the presence of LiHMDS was developed. Both unreactive electron-rich fluoroarenes and electron-poor fluoroarenes proceeded smoothly and afforded the cor

Enhanced catalytic activity of CuI/diethoxyphosphoryl-1,10-phenanthrolines in ‘on water’ Cu-catalyzed Sonogashira reaction

The use of CuI/diethoxyphosphoryl-1,10-phenanthrolines and ‘on water’ conditions in the Cu-catalyzed Sonogashira reaction of aryl iodides with terminal alkynes significantly increases the reaction rate as compared to that in organic solvents.

Sonogashira Cross-Coupling of Aryltrimethylammonium Salts

A protocol for C(sp)-C(sp2) bond formation via the Sonogashira coupling reaction involving C-N bond cleavage with aryltrimethylammonium triflate as an electrophilic coupling partner is described in this work. The reactions proceeded well under mild conditions with a stoichiometric ratio of alkyl, aryl, or heteroaryl acetylenes and provided yields of up to 93%. Numerous useful functional groups were tolerated under the reaction conditions. Direct amine alkynylation can be achieved through a one-pot process without the isolation of ammonium salt. The protocol can be performed on a gram scale. Density functional theory calculations were performed to investigate the reaction mechanism that involved oxidative addition, alkyne coordination, deprotonation, and reductive elimination, which yielded the cross-coupling product.

A novel zinc-catalyzed Suzuki-type cross-coupling reaction of aryl boronic acids with alkynyl bromides

A novel Suzuki-type cross-coupling reaction of organoboron reagents with alkynyl bromides has been developed in the presence of catalytic Et2Zn/DMEDA system. The reaction afforded a variety of internal alkynes in moderate to excellent yields under mild reaction conditions without the formation of any homo-coupling products. The resulting internal alkynes have valuable applications in pharmaceutical and industrial areas. The use of relatively non-toxic zinc, chelating amine ligand and low reaction temperature make this protocol an alternative for the synthesis of internal alkynes. The scope and limitations of this protocol are also investigated.

Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes

Carbon-carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C-C cross-coupling reaction of two kinds of organic halide, a gem -dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination-hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.