Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamideviaa one-pot sequential aminolysis-sulfation reaction of (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO)

Herrlé, Chloé; Toumieux, Sylvestre; Araujo, Maryne; Peru, Aurélien; Allais, Florent; Wadouachi, Anne

doi:10.1039/d2gc01345b

Cited by 5 publications

(8 citation statements)

References 36 publications

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“…In 2022, Wadouachi et al reported the one-pot/two-step mechanochemical synthesis of four potential surfactants (4 S )- N -alkyl-4,5-bis-sulfooxypentanamides 29 from bio-based ( S )-γ-hydroxymethyl-γ-butyrolactone 27 (2H-HBO) in a one-pot two-step process (Scheme 7). 86 This short sequence consisted of an aminolysis of 2H-HBO 27 followed by a disulfation reaction using a PBM. The optimized conditions consisted of grinding 2H-HBO (1 equiv.)…”

Section: Green Metrics Used In Mechanochemical Reactionsmentioning

confidence: 99%

Green metrics in mechanochemistry

Fantozzi,

Volle,

Porcheddu

et al. 2023

Chem. Soc. Rev.

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Section: Green Metrics Used In Mechanochemical Reactionsmentioning

confidence: 99%

Green metrics in mechanochemistry

Fantozzi,

Volle,

Porcheddu

et al. 2023

Chem. Soc. Rev.

View full text Add to dashboard Cite

show abstract

“…In 2022, Wadouachi et al reported the one-pot/two-step mechanochemical synthesis of four potential surfactants (4S)-N-alkyl-4,5-bis-sulfooxypentanamides 29 from bio-based (S)-γhydroxymethyl-γ-butyrolactone 27 (2H-HBO) in a one-pot twostep process (Scheme 7). 58 This short sequence consisted in of an aminolysis of 2H-HBO 27 followed by a disulfation reaction using a PBM. The optimized conditions consisted on grinding 2H-HBO (1 equiv.)…”

Section: Scheme 5: Amidification Synthesis With CDI In Mechanochemistrymentioning

confidence: 99%

Green metrics in Mechanochemistry

Fantozzi

Volle

Porcheddu

et al. 2022

Preprint

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The development of new green methodologies and their broader adoption for promoting sustainable development in chemistry laboratories and industry play a significant role in society, due to the economic importance of chemistry and its and widespread presence in everyday life. Therefore, a sustainable approach to chemistry contributes to the well-being of worldwide population and comply with the United Nations Sustainable Development Goals (UN SDGs) and the European Green Deal. The review highlights how mechanochemical methods in batch and in continuous are an eco-friendly approach for organic synthesis, with a lower environmental footprint in most cases, compared to solution-based procedures. The assessment is objectively based on the use of green metrics (e.g. atom and real atom economy, E-factor, Process Mass Intensity, Material Parameter Recovery, Eco-scale, Stoichiometric Factor, etc.) and indicators (e.g. DOZN tool and Life Cycle Assessment, LCA, studies) applied to organic transformations such as synthesis of amide bond, carbamates, heterocycles, Active Pharmaceutical Ingredients (APIs), porphyrins, Porous Organic Polymers (POPs), metal- or acid-catalysed processes, multicomponent and condensation reactions, rearrangements, etc. The generalized absence of bulk solvents, the precise control over the stoichiometry (i.e., using agents in a stoichiometrically rather than in excess), and the more selective reactions enabling simplified work-up procedures are the distinctive factors marking the superiority of mechanochemical processes over solution-based chemistry.

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“…13 Furthermore, the development of a one-pot two-step strategy for the mechanosynthesis of anionic surfactants was also effective with LGOderived (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO (1), Scheme 1) in a planetary ball mill. 14 Indeed, leveraging our expertise in LGO chemistry, we capitalized on biobased lactone 1, which can be easily derived from LGO. 15 Through a mechanochemical transformation, lactone 1 was converted into various diols via an aminolysis reaction with different primary amines.…”

Section: Introductionmentioning

confidence: 99%

“…13 Furthermore, the development of a one-pot two-step strategy for the mechanosynthesis of anionic surfactants was also effective with LGO-derived ( S )-γ-hydroxymethyl-γ-butyrolactone (2H-HBO ( 1 ), Scheme 1) in a planetary ball mill. 14…”

Section: Introductionmentioning

confidence: 99%

“…15 Through a mechanochemical transformation, lactone 1 was converted into various diols via an aminolysis reaction with different primary amines. 14 This reaction was carried out under stoichiometric conditions in a planetary ball mill using zirconium jars and balls. A series of N -alkyl-amide derivatives was obtained in 8 cycles (each cycle consisting of 5 min with a 1 min pause between cycles) at 400 rpm, achieving excellent conversions (88 to >97%) and good yields (62 to 76%) (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

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