15852-01-4

Upstream product

• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 873-73-4 4-n-chlorophenylacetylene 
• 586-78-7 para-nitrophenyl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 636-98-6 p-nitrobenzene iodide 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 
• 100-00-5 4-chlorobenzonitrile 
• 5281-22-1 1-(2,2-dichlorovinyl)-4-nitrobenzene 
• 5575-51-9 tris(4-chlorophenyl)bismuthane 
• 555-16-8 4-nitrobenzaldehdye 
• 2287-78-7 tetra(4-chlorophenylethynyl)tin 
• 1679-18-1 4-Chlorophenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 15851-77-1 {4-[(4-chlorophenyl)ethynyl]phenyl}amine 
• 14064-70-1 (Z)-(4-chlorophenyl)(4'-nitrophenyl)ethene 
• 168151-97-1 N-[4-(4-Chloro-phenylethynyl)-phenyl]-2-cyano-acetamide 
• 168151-99-3 (Z)-(4-aminophenyl)(4'-chlorophenyl)ethene 
• 168151-98-2 N-{4-[(Z)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-2-cyano-acetamide 

Relevant academic research and scientific papers

Aerobic Cu and amine free Sonogashira and Stille couplings of aryl bromides/chlorides with a magnetically recoverable Fe3O4@SiO2 immobilized Pd(II)-thioether containing NHC

Two value added C–C cross coupling reactions; Sonogashira and Stille couplings were achieved at milder conditions in the catalytic presence of a magnetically recoverable heterogeneous catalyst Fe3O4@SiO2@NHC^SPh-Pd(II). The catalyst was earlier reported for Suzuki-Miyaura reaction, and as an extension of its catalytic efficiency, the Stille and Sonogashira cross coupling reactions under aerobic condition has been explored in present report. The Sonogashira coupling of aryl bromides and terminal alkynes produced an excellent yield (~96% at 0.25 mol% Pd) of the desired coupling product under copper and amines free conditions. Moreover, an excellent Stille coupling of readily available and more latent aryl chlorides and trialkylstannane was obtained (yields up to 95% at 0.25 mol% Pd) in absence of toxic fluorides additives. The broad substrate scope of the catalyst for both the coupling reactions and the magnetically recoverable feature of catalyst make this reaction highly desirable for industrial applications of present heterogeneous catalysis.

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

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.

Synthesis of Diarylacetylenes Bearing Electron-Withdrawing Groups via the Smiles Rearrangement

Nitrobenzyl benzothiazol-2-yl sulfones and nitrobenzyl 1-phenyl-1 H -tetrazol-5-yl sulfones react with chlorides of aromatic acids to form β-acyl derivatives. These products undergo the Smiles rearrangement resulting in the formation of the corresponding nitrophenyl arylacetylenes in 50-60% overall yields (approx. 75% per step). Sulfones bearing CF 3 or CN groups instead of a NO 2 substituent form mixtures of the acetylenes in moderate yields and benzyl aryl ketones in yields above 40%.

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

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.

Tetraalkynylstannanes in the Stille cross coupling reaction: a new effective approach to arylalkynes

The Stille-type cross coupling reaction with tetraalkynylstannanes was studied in detail for the first time. The reaction provides a simple and effective route towards a variety of arylalkynes. The advantages and limitations of the proposed procedure are discussed.

Efficient Sonogashira and Suzuki-Miyaura coupling reaction catalyzed by Pd-Nanoparticles

The Pd nano particles were electrochemically deposited on nafion-graphene. They showed excellent catalytic activity towards Sonogashira and Suzuki-Miyaura cross-coupling reaction. Benzenediazonium salts were used as alternative to aromatic halide. The developed protocol offers recyclability, easy workups with short reaction time and good-to-excellent product yield. [Figure not available: see fulltext.]

Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling

A dual photoredox and gold-catalysed cross-coupling reaction of alkynyltrimethylsilanes and aryldiazonium tetrafluoroborates is described. The reaction proceeds through visible-light mediated oxidative addition of aryldiazoniums, transmetalation of alkynyltrimethylsilanes and aryl-alkynyl reductive elimination. Exclusive selectivity for silyl-substituted alkynes is observed, with no reactivity observed for terminal alkynes.