16616-42-5

Upstream product

• 106-39-8 bromochlorobenzene 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 102990-14-7 1-(4-chlorophenyl)-3-phenylprop-2-yn-1-ol 
• 104-88-1 4-chlorobenzaldehyde 
• 64-18-6 formic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 124-38-9 carbon dioxide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 3757-88-8 tributylstannylethynylbenzene 

Downstream Products

• 75371-73-2 (Z)-1-p-chlorophenyl-3-phenyl-3-piperidino-prop-2-en-1-one 
• 75371-74-3 (Z)-3-morpholino-1-p-chlorophenyl-3-phenyl-prop-2-en-1-one 
• 75371-74-3 (Z)-1-(4-Chloro-phenyl)-3-morpholin-4-yl-3-phenyl-propenone 
• 53324-04-2 (E,Z)-3,3'-Thiodi(1-p-chlorophenyl-3-phenylprop-2-en-1-one) 
• 115665-13-9 (4-Chloro-phenyl)-(3,5-diphenyl-isoxazol-4-yl)-methanone 
• 122942-52-3 (4-Chloro-phenyl)-[3-(4-nitro-phenyl)-5-phenyl-3H-[1,2,3]triazol-4-yl]-methanone 
• 122942-44-3 (4-Chloro-phenyl)-[1-(4-nitro-phenyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-methanone 
• 95734-18-2 3,6-Bis-(4-chloro-phenyl)-4-phenyl-1H-pyridin-2-one 
• 122942-57-8 (4-Chloro-phenyl)-[3-(4-methoxy-phenyl)-5-phenyl-3H-[1,2,3]triazol-4-yl]-methanone 
• 122942-49-8 (4-Chloro-phenyl)-[1-(4-methoxy-phenyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-methanone 
• 95772-50-2 6-(4-Chloro-phenyl)-3-(4-methoxy-phenyl)-4-phenyl-1H-pyridin-2-one 
• 73486-37-0 2-(4-chlorobenzoylmethyl)-5-methyl-2-phenyl-1,3-benzodithiole 
• 76203-63-9 1-(p-Chlorphenyl)-3-phenyl-3-isothiocyano-prop-2-ene-1-one 
• 53324-02-0 (Z,Z)-3,3'-Thiodi(1-p-chlorophenyl-3-phenyl-prop-2-ene-1-one) 

Relevant academic research and scientific papers

Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6

A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.

Using Pd-salen complex as an efficient catalyst for the copper- and solvent-free coupling of acyl chlorides with terminal alkynes under aerobic conditions

The palladium-salen complex palladium(II) N,N′-bis{[5-(triphenylphosphonium)-methyl]salicylidene}-1,2-ethanediamine chloride was found to be a highly active catalyst for the copper- and solvent-free coupling reaction of terminal alkynes with different acy

Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia

(Matrix presented) Carbonylative coupling of phenylethyne with 4-methoxy-1-iodobenzene in the presence of 1 mol% PdCl2(PPh 3)2, 2 equiv of 0.5 M aqueous ammonia, and CO (1 atm) gives the corresponding α,β-alkynyl ketone in

Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents

A first observation of the direct alkynyl group transfer from silicon to copper is reported. The silicon group of alkynylsilanes was smoothly replaced by copper (I) chloride in DMI to give the corresponding copper (I) acetylides. This transformation was a

Palladium nanoparticles supported on Smopex metal scavengers as catalyst for carbonylative Sonogashira reactions: Synthesis of α,β-alkynyl ketones

Palladium nanoparticles supported on two Smopex commercial metal scavengers (1% w/w) have been tested in the carbonylative Sonogashira reactions of aryl iodides with phenylacetylene. Their catalytic activity has been compared with those of more common catalysts (Pd/C, Pd/γ-Al 2O3). Pd/Smopex-234 resulted especially effective in the synthesis of alkynyl ketones even working with a low amount of palladium (0.2-0.5 mol%). Preliminary heterogeneity tests (i.e. hot filtration test, Pd leaching and recycle of the catalyst) have been performed in order to evaluate the catalytic behaviour of this system. The obtained results seem to indicate that Pd/Smopex-234 could act as a truly heterogeneous catalyst.

Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes

Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de

Feeding Carbonylation with CO2via the Synergy of Single-Site/Nanocluster Catalysts in a Photosensitizing MOF

Solar-driven carbonylation with CO2 replacing toxic CO as a C1 source is of considerable interest; however it remains a great challenge due to the inert CO2 molecule. Herein, we integrate cobalt single-site and ultrafine CuPd nanocluster catalysts into a

Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones

Oxidative carbonylation using carbon monoxide has evolved as an attractive tool to valuable carbonyl-containing compounds, while mixing CO with a stoichiometric amount of a chemical oxidant especially oxygen is hazardous and limits its application in scale-up synthesis. By employing anodic oxidation, we developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism of the electrochemical Pd(0)/Pd(II) cycle is rationalized based upon cyclic voltammetry, kinetic studies, and intermediates experiments.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source

Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.