Carbonylative Sonogashira Coupling Research Articles

Synthesis of ferrocene-labelled steroid derivatives via homogeneous catalytic methods

Carbonylative Sonogashira coupling and copper catalyzed azide–alkyne cycloaddition were used effectively in the synthesis of ferrocene-labelled steroids. Steroidal alkynyl ketones were obtained in moderate yield from 17-ethynyl steroids without the necessity for the protection of the 17β-OH group of various compounds. Unfortunately, the alkynyl ketone derivatives could not be converted to steroids with heterocyclic groups at C-17 using methylhydrazine cyclocondensation agent. At the same time, 17-triazolyl steroids with ferrocene labels were synthesized in excellent yields starting from the same substrates by a copper-catalyzed azide alkyne cycloaddition. The new compounds were characterized by 1H and 13C NMR, MS and IR.

Convenient and General Palladium‐Catalyzed Carbonylative Sonogashira Coupling of Aryl Amines

Bar (alky)none: A general and efficient method for carbonylative Sonogashira coupling reactions of anilines to generate alkynones has been developed (see scheme; TFP=tri(2-furyl)phosphine). The reaction proceeds under mild conditions and no base is needed.

Convenient and General Palladium‐Catalyzed Carbonylative Sonogashira Coupling of Aryl Amines

Alkinone auf einfache Tour: Eine allgemeine und effiziente Methode für die carbonylierende Sonogashira-Kupplung von Anilinen zur Bildung von Alkinonen wurde entwickelt (siehe Schema; TFP=Tri(2-furyl)phosphan). Die Reaktion verläuft unter milden Bedingungen und erfordert keine Base.

ChemInform Abstract: Cross‐Linked Polymer‐Supported Palladium‐Catalyzed Carbonylative Sonogashira Coupling Reaction in Water.

Abstract A cross-linked polymer-supported ionic liquid immobilized palladium catalyst, which is prepared by reaction of the Pd(OAc)2 with copolymer of 3-butyl-1-vinylimidazolium iodide and divinylbenzene, was well characterized and employed as an effective heterogeneous catalyst for carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes in water, affording the corresponding α,β-alkynyl ketones in good to excellent yields. The catalytic system not only solves the basic problem of homogeneous palladium catalyst recovery and reuse but also avoids the use of toxic phosphine ligands. The stability of supported palladium was also discussed.

ChemInform Abstract: A General Palladium‐Catalyzed Carbonylative Sonogashira Coupling of Aryl Triflates.

AbstractThe present new method for carbonylative Sonogashira reactions of aryl triflates with alkynes results in the formation of alkynones which are useful building blocks for the synthesis of biologically active compounds.

Cross-linked polymer supported palladium catalyzed carbonylative Sonogashira coupling reaction in water

A cross-linked polymer-supported ionic liquid immobilized palladium catalyst, which is prepared by reaction of the Pd(OAc)2 with copolymer of 3-butyl-1-vinylimidazolium iodide and divinylbenzene, was well characterized and employed as an effective heterogeneous catalyst for carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes in water, affording the corresponding α,β-alkynyl ketones in good to excellent yields. The catalytic system not only solves the basic problem of homogeneous palladium catalyst recovery and reuse but also avoids the use of toxic phosphine ligands. The stability of supported palladium was also discussed.

Palladium-catalyzed carbonylative coupling of benzyl chlorides with terminal alkynes to give 1,4-diaryl-3-butyn-2-ones and related furanones

A general palladium-catalyzed carbonylative Sonogashira coupling of benzyl chlorides with terminal acetylenes has been established. Depending on the alkyne 1,4-diaryl-3-butyn-2-ones or substituted furanones are obtained in moderate to good yields. Best catalytic performance is achieved applying a mixed Pd(PPh(3))Cl(2)/P(OPh)(3) catalyst system.

A General Palladium‐Catalyzed Carbonylative Sonogashira Coupling of Aryl Triflates

Trifling with triflates: A new protocol for the carbonylative Sonogashira reactions of aryl triflates (see scheme) that provides a significant extension of this interesting methodology is described.

A General and Convenient Palladium‐Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides

A variety of aromatic bromides and aromatic terminal alkynes are reacted to afford the products with good yields.

A two-step synthesis of ferrocenyl pyrazole and pyrimidine derivatives based on carbonylative Sonogashira coupling of iodoferrocene

A new method for the synthesis of 3-substituted-1-ferrocenyl-2-propyn-1-ones was developed involving carbonylative Sonogashira coupling of iodoferrocene with terminal acetylenes. New ferrocenyl 1,3,5-trisubstituted pyrazoles and 2,4,6-trisubstituted pyrimidines were obtained by the addition-cyclocondensation reaction of the alkynones with hydrazines and guanidinium salts, respectively. The products were obtained with moderate to excellent yields and were characterised with various spectroscopic methods ( 1H NMR, 13C NMR IR, MS).

ChemInform Abstract: Magnetically Separable Pd Catalyst for Carbonylative Sonogashira Coupling Reactions for the Synthesis of α,β‐Alkynyl Ketones.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The first heterogeneous carbonylative Sonogashira coupling reaction catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex

The first heterogeneous carbonylative Sonogashira coupling reaction of terminal alkynes with aryl iodides under atmospheric pressure of carbon monoxide was achieved in the presence of a catalytic amount of MCM-41-supported bidentate phosphine palladium(0) complex [MCM-41-2P-Pd(0)] in good to high yields. This polymeric palladium catalyst can be reused at least 10 times without any decrease in activity.

Magnetically Separable Pd Catalyst for Carbonylative Sonogashira Coupling Reactions for the Synthesis of α,β-Alkynyl Ketones

A magnetically separable palladium catalyst was simply synthesized through a wet impregnation incorporating palladium nanoparticles and superparamagnetic Fe3O4 nanoparticles in KBH4 solution, which is a highly efficient catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes under phosphine-free conditions. This catalyst is completely magnetically recoverable due to the super paramagnetic behavior of Fe3O4 and can be reused with sustained selectivity and activity.

ChemInform Abstract: Copper‐Catalyzed, Palladium‐Free Carbonylative Sonogashira Coupling Reaction of Aliphatic and Aromatic Alkynes with Iodoaryls.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Copper-Catalyzed, Palladium-Free Carbonylative Sonogashira Coupling Reaction of Aliphatic and Aromatic Alkynes with Iodoaryls

Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed carbonylative Sonogashira coupling reactions of aliphatic/aromatic alkynes with iodoaryls are reported for the first time. The protocol eliminates the use of a toxic, air-sensitive, and expensive Pd-phosphine-based catalytic system, and provides high yields of desired products.

A simple and efficient recyclable phosphine-free catalytic system for alkoxycarbonylation and carbonylative Sonogashira coupling reactions of aryl iodides

Using palladium on charcoal (Pd/C) and triethylamine as a novel, efficient, versatile, recyclable, and phosphine-free catalytic system, we carried out the alkoxycarbonylation of aryl iodides (alcohols or phenols as nucleophiles) and the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes, affording the corresponding aryl esters and α , β -alkynyl ketones in good to excellent yields under mild conditions. We found that both electron-withdrawing and electron-donating substituents on phenol enhanced the phenoxycarbonylation of iodobenzene. The recyclability of Pd/C was also demonstrated.

One-Pot Synthesis of 2,5-Disubstituted Oxazoles

Reported is a concise one-pot three-step amidation, Pd-catalyzed acylation, and cycloisomerization procedure for the synthesis of 1-(hetero)aryl-2-[2-(hetero)aryloxazol-5-yl] ethanones from propargyl amine and acid chlorides in moderate to good overall yields. Anhydrides may be used as replacements of acid chlorides in the first step allowing access to 2-trifluoromethyl derivatives; carbonylative Sonogashira coupling can be used equally well in the second step. The structures have been confirmed by X-ray crystal structure analysis of one of the products.

Low Pressure Pd‐Catalyzed Carbonylation in an Ionic Liquid Using a Multiphase Microflow System.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Low pressure Pd-catalyzed carbonylation in an ionic liquid using a multiphase microflow system

A low pressure microflow system was developed for palladium-catalyzed multiphase carbonylation reactions in an ionic liquid. The microflow system resulted in superior selectivity and higher yields in carbonylative Sonogashira coupling and amidation reactions of aryl iodides compared to the conventional batch system.

Palladium-Catalyzed Multicomponent Synthesis of Pyrazoles and Isoxazoles

The palladium-catalyzed four-component coupling of terminal alkynes, hydrazines or hydroxylamine, carbon monoxide, and aryl iodides to furnish pyrazole or isoxazole derivatives is reported. The reaction is regioselective and proceeds at room temperature and at ambient pressure of carbon monoxide in aqueous THF. The reaction involves sequential carbonylative Sonogashira coupling followed by a cyclization reaction of hydrazine or hydroxylamine with the formed α,β-alkynyl ketones. Hydroxylamine may also be used in place of hydrazine to give isoxazole derivatives.