Lipids as versatile solvents for chemical synthesis

Gevorgyan, Ashot; Hopmann, Kathrin H.; Bayer, Annette

doi:10.1039/d1gc02311j

Cited by 11 publications

(6 citation statements)

References 78 publications

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“… 270 For example, cross-coupling can be successfully conducted in rapeseed oil and butter with both of these lipid-based systems outperforming benchmark solvent DMF. 271 …”

Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

“…Note that discussion surrounding the use of Suzuki-Miyaura reactions as a benchmark for the performance of new solvents suggests that it is not the most informative reaction manifold . For example, cross-coupling can be successfully conducted in rapeseed oil and butter with both of these lipid-based systems outperforming benchmark solvent DMF …”

Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

“…268 For example, cross-coupling can be successfully conducted in rapeseed oil and butter with both of these lipidbased systems outperforming benchmark solvent DMF. 269 Watson and co-workers developed a mild method for the Suzuki-Miyaura reaction that employed Cyrene as a greener alternative to the commonly used dipolar aprotic solvents (Scheme 16). 14 Yields for a series of reactions performed in both NMP and NBP have been reported, to carry out a comparison, using a range of different substituted aryl halides to explore the scope.…”

Section: Amide Bond Formationmentioning

confidence: 99%

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Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N -methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

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“… 270 For example, cross-coupling can be successfully conducted in rapeseed oil and butter with both of these lipid-based systems outperforming benchmark solvent DMF. 271 …”

Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

Section: Amide Bond Formationmentioning

confidence: 99%

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Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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“…The idea of organic syntheses using safe, renewable and low‐cost solvents has been a challenge increasingly pursued in chemistry laboratories for many years 22 . Recent reports describe the efficient use of vegetable oils, waxes or even butter in Suzuki‐Miyaura, Hiyama, Stille, Sonogashira and Heck cross‐couplings 23 . In turn, the use of untypical solvents for ATRP has recently been gaining popularity in an attempt to develop unconventional solutions that could be applied in the production of polymers on an industrial scale 24 .…”

Section: Introductionmentioning

confidence: 99%

“…22 Recent reports describe the efficient use of vegetable oils, waxes or even butter in Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings. 23 In turn, the use of untypical solvents for ATRP has recently been gaining popularity in an attempt to develop unconventional solutions that could be applied in the production of polymers on an industrial scale. 24 The presence of salt in sea water ([NaCl] 0 = 437 mM and [NaBr] 0 = 0.50 mM), which participates in the ATRP process as a supporting electrolyte, has been successfully exploited.…”

Section: Introductionmentioning

confidence: 99%

Red is the new green: Dry wine‐based miniemulsion as eco‐friendly reaction medium for sustainable atom transfer radical polymerization

Flejszar

Chmielarz

Oszajca

2022

J of Applied Polymer Sci

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Wine‐based miniemulsion was used as polymerization medium for the synthesis of non water‐miscible polymethacrylates for the first time. The solution, inspired by green chemistry principles, is an interesting alternative to the use organic solvent application in polymer synthesis. The paper presents an unusual but cost‐effective solution, which, due to the presence of reducing agents present in wine, allowed the synthesis of polymethacrylates according to the low ppm atom transfer radical polymerization (ATRP) concept, but without the injection of additional reducing agents. Among the tested liquors were: (a) a white semi‐sweet wine (Tokaj—TK); (b) ruby sweet wine (Carlo Rossi—CR); (c) raspberry homemade wine (Wino Jana—WJ), and (d) dark red dry wine (Merlot—ME). Interestingly, the use of dry wine with ~300 ppm by wt of CuII/tris(2‐pyridylmethyl) amine (TPMA) as hydrophilic catalyst resulted in the controlled synthesis of poly(n‐butyl acrylate) (PnBA), poly(n‐butyl methacrylate) (PnBMA), and poly(tert‐butyl acrylate) (PtBA) characterized by a narrow molecular weight distribution (Đ = 1.18–1.50). The final structures of the synthesized polymers were comprehensively analyzed by attenuated total reflectance Fourier transform infrared spectroscopy (ATR‐FTIR), proton nuclear magnetic resonance spectroscopy (1H NMR), dynamic light scattering (DLS), and scanning electron microscopy (SEM).

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Aryl/Hetero‐Aryl Tosylates as Coupling Partners in Metal‐Mediated Suzuki and Hiyama Cross‐Coupling Reactions in Ionic Liquids: Ligand‐Free Facile Synthesis of Biaryls/Heterobiaryls

Jadhav,

Kurahatti,

Anchi

et al. 2024

ChemistrySelect

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Diverse libraries of biaryls/heterobiaryls were synthesized by aryl/hetero‐aryl tosylates as coupling partners in the ligand‐free, Ni‐catalyzed Suzuki coupling reaction, and Pd‐catalyzed Hiyama cross‐coupling reaction in ionic liquids (ILs) as green solvent. In this method easily available and economically viable tosylates were coupled with readily available boronic acids and phenyltriethoxysilanes in Suzuki and Hiyama cross‐coupling respectively to yield the corresponding biaryls/heterobiaryls. Mild reaction condition(s), easy workup, moderate to excellent yield of the isolated pure products, wide substrate scope, and recycling/reuse of the ILs are the advantages of this method over the other reported methods.

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Lipids as versatile solvents for chemical synthesis

Abstract: Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis....

Cited by 11 publications

References 78 publications

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Red is the new green: Dry wine‐based miniemulsion as eco‐friendly reaction medium for sustainable atom transfer radical polymerization

Aryl/Hetero‐Aryl Tosylates as Coupling Partners in Metal‐Mediated Suzuki and Hiyama Cross‐Coupling Reactions in Ionic Liquids: Ligand‐Free Facile Synthesis of Biaryls/Heterobiaryls

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