Palladium‐catalysed cyclocarbonylation reactions in dimethyl carbonate, an eco‐friendly solvent and ring‐opening reagent

Vasapollo, Giuseppe; Mele, Giuseppe; Maffei, Annamaria; Sole, Roberta Del

doi:10.1002/aoc.543

Cited by 38 publications

(13 citation statements)

References 30 publications

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“…Carbonates have been employed successfully for somec lassical metal-catalyzed reactions such as enantioselective hydrogenation, [17] alkene metathesis, [18] carbonylation, [19] oxidation, [20] hydroxylation, [21] Sonogashira coupling, [22] Heck vinylation or allylic alkylation, [23] and CÀHb ond activation/functionalization.…”

Section: Introductionmentioning

confidence: 99%

Eco‐Friendly Solvents for Palladium‐Catalyzed Desulfitative CH Bond Arylation of Heteroarenes

et al. 2015

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Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.

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Section: Introductionmentioning

confidence: 99%

Eco‐Friendly Solvents for Palladium‐Catalyzed Desulfitative CH Bond Arylation of Heteroarenes

et al. 2015

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“…DMC is used in the chemical industry as monomer for polymers, in transesterification reactions for the production of other carbonates such as diphenylcarbonate and others, as alkylating or carboxylating agent . It is also used in the agrochemical and pharmaceutical industry for the production of chemicals or in product formulation. A new potential application of DMC is as an additive to gasoline that would expand its utilization by almost two orders of magnitude.…”

Section: Synthesis Of Linear Carbonatesmentioning

confidence: 99%

Use of carbon dioxide as feedstock for chemicals and fuels: homogeneous and heterogeneous catalysis

Dibenedetto

Angelini

Stufano

2013

J of Chemical Tech & Biotech

199

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CO2 is considered to play a key role in an eventual climate change, due to its accumulation in the atmosphere. The control of its emission represents a challenging task that requires new ideas and new technologies. The use of perennial energy sources and renewable fuels instead of fossil fuels and the conversion of CO2 into useful products are receiving increased attention. The utilization of CO2 as a raw material for the synthesis of chemicals and fuels is an area in which scientists and industrialists are much involved: the implementation of such technology on a large scale would allow a change from a linear use of fossil carbon to its cyclic use, mimicking Nature. In this paper the use of CO2 as building block is discussed. CO2 can replace toxic species such as phosgene in low energy processes, or can be used as source of carbon for the synthesis of energy products. The reactions with dihydrogen, alcohols, epoxides, amines, olefins, dienes, and other unsaturated hydrocarbons are discussed, under various reaction conditions, using metal systems or enzymes as catalysts. The formation of products such as formic acid and its esters, formamides, methanol, dimethyl carbonate, alkylene carbonates, carbamic acid esters, lactones, carboxylic acids, and polycarbonates, is described. The factors that have limited so far the conversion of large volumes of CO2 are analyzed and options for large‐scale CO2 catalytic conversion into chemicals and fuels are discussed. Both homogeneous and heterogeneous catalysts are considered and the pros and cons of their use highlighted. © 2013 Society of Chemical Industry

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“…In particular, if the cyclocarbonylation reaction of allylphenols was performed in DMC, yield and regioselectivity of seven-membered ring lactone were similar to those obtained performed in toluene under analogous reaction conditions (Scheme 32). Differently to the other solvents, DMC at high temperature and longer reaction time behaved as reactant, promoting the formation of methoxycarbonyl compounds [40]. The homogeneous catalytic system Pd(OAc)2 -dppb was shown to be an active catalyst also for double cyclocarbonylation reactions of bis-allyl phenols to the corresponding bis-lactones.…”

Section: Five- Six-and Seven-membered and Bis-lactones Fused To Arommentioning

confidence: 99%

Synthesis of Heterocycles by Transition Metals-Catalyzed Cyclocarbonylation Reactions

Vasapollo

Mele

2006

COC

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The synthesis of heterocyclic compounds such as lactones, lactams, pyrrolidinones and others can be achieved by cyclocarbonylation reactions catalyzed by transition metal complexes. The combination of palladium salts with certain different ligands turned out to be the most efficient catalyst systems to accomplish such cyclocarbonylation reactions. New synthetic strategies and novel approaches devoted to the preparation of such compounds having different ring size still remain a stimulating area of academic and industrial research.

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Palladium‐catalysed cyclocarbonylation reactions in dimethyl carbonate, an eco‐friendly solvent and ring‐opening reagent

Cited by 38 publications

References 30 publications

Eco‐Friendly Solvents for Palladium‐Catalyzed Desulfitative CH Bond Arylation of Heteroarenes

Eco‐Friendly Solvents for Palladium‐Catalyzed Desulfitative CH Bond Arylation of Heteroarenes

Use of carbon dioxide as feedstock for chemicals and fuels: homogeneous and heterogeneous catalysis

Synthesis of Heterocycles by Transition Metals-Catalyzed Cyclocarbonylation Reactions

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