Towards a sustainable synthesis of amides: chemoselective palladium-catalysed aminocarbonylation of aryl iodides in deep eutectic solvents

Messa, Francesco; Perrone, Serena; Capua, Martina; Tolomeo, Francesco; Troisi, Luigino; Capriati, Vito; Salomone, Antonio

doi:10.1039/c8cc03858a

Cited by 69 publications

(44 citation statements)

References 56 publications

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“…Within the framework of green chemistry, solvents occupy a strategic place, and in the literature, novel approaches have also been proposed, addressing the use of safer alternative media for this kind of transformation. Ramesh et al employed an acidic ionic liquid as a reusable catalyst for the reaction of furfural and secondary amines to yield trans -4,5-diaminocyclopent-2-enones [ 19 ], and our group recently demonstrated the successful use of water as a reaction medium for the preparation of cyclopentenone derivatives under microwave irradiation [ 20 , 21 ]. In addition, a very recent paper from Afonso’s group described the use of Cu(OTf) 2 as a very efficient catalyst for the synthesis of cyclopentenones in water at room temperature for only 1 min [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

et al. 2018

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The development of novel synthetic routes to produce bioactive compounds starting from renewable sources has become an important research area in organic and medicinal chemistry. Here, we present a low-cost procedure for the tunable and selective conversion of biomass-produced furfural to cyclopentenone derivatives using a mixture of choline chloride and urea as a biorenewable deep eutectic solvent (DES). The proposed medium is a nontoxic, biodegradable, and could be reused up to four times without any unfavorable effect on the reaction yield. The process is tunable, clean, cheap, simple and scalable and meets most of the criteria; therefore, it can be considered as an environmental sustainable process in a natural reaction medium.

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Section: Introductionmentioning

confidence: 99%

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

et al. 2018

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“…Because of their ability to act also as catalysts and reagents [29,30], DESs have been primarily investigated in extraction and separation processes [31][32][33][34], in material sciences [35], for metal electrodeposition [36], and for the synthesis of heterocycles [37]. Emerging and hot fields of applications are represented by organometallics [38][39][40], metal- [41][42][43][44][45][46][47][48], bio- [49][50][51][52][53], and organo-catalysis [54][55][56][57], electrochemistry [58], photosynthesis [59] and energy technology [60,61]. Building upon our interests in the synthesis of drugs and heterocycles using eco-friendly reaction media like DESs [43][44][45][46][47]55,62,63] and water [64], herein we report the sustainable preparation of several 2-hydroxyphenylbenzimidazole derivatives and the whole synthesis of PZ1 [19] in selected eutectic mixtures.…”

Section: Introductionmentioning

confidence: 99%

Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds

et al. 2020

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An unsubstituted 2-hydroxyphenylbenzimidazole has recently been included as a scaffold in a series of hybrids (including the hit compound PZ1) based on the framework of the acetylcholinesterase (AChE) inhibitor Donepezil, which is a new promising multi-target ligand in Alzheimer’s disease (AD) treatment. Building upon these findings, we have now designed and completed the whole synthesis of PZ1 in the so-called deep eutectic solvents (DESs), which have emerged as an unconventional class of bio-renewable reaction media in green synthesis. Under optimized reaction conditions, the preparation of a series of 2-hydroxyphenylbenzimidazole-based nuclei has also been perfected in DESs, and comparison with other routes which employ toxic and volatile organic solvents (VOCs) provided. The functionalization of the aromatic ring can have implications on some important biological properties of the described derivatives and will be the subject of future studies of structure-activity relationships (SARs).

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“…For such cases, it may be necessary to design new catalysts that are compatible with the reaction medium, albeit metal‐catalyzed reactions in DES using cheap and commercially available catalysts [e.g. Pd/C or Pd(OAc) 2 ] have been reported . Even though solvents are important in some reactions modulating or even influencing their outcome, if possible carrying out chemical transformations in the absence of solvent is convenient from an environmental point of view .…”

Section: Introductionmentioning

confidence: 99%

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

2019

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Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2‐aminobenzaldehydes and 2‐aminoaryl ketones under solvent‐free conditions, employing 1,3‐bis(carboxymethyl)‐imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3‐acetylquinolines have been transformed, under solvent‐free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E‐factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

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Towards a sustainable synthesis of amides: chemoselective palladium-catalysed aminocarbonylation of aryl iodides in deep eutectic solvents

Cited by 69 publications

References 56 publications

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

Deep Eutectic Solvents as Effective Reaction Media for the Synthesis of 2-Hydroxyphenylbenzimidazole-Based Scaffolds en Route to Donepezil-Like Compounds

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

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