Direct Amidation of Esters by Ball Milling**

Nicholson, William I.; Barreteau, Fabien; Leitch, Jamie A.; Payne, Riley; Priestley, Ian; Godineau, Edouard; Battilocchio, Claudio; Browne, Duncan L.

doi:10.1002/anie.202106412

Cited by 67 publications

(57 citation statements)

References 124 publications

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“…Noteworthy, chemists in industry are showing an increased interest in mechanochemistry. [33] Once widely adopted, because of the drastic reduction of the amount of organic solvents used, this strategy will contribute decisively to the development of sustainable chemistry with a positive impact on the environment.…”

Section: Discussionmentioning

confidence: 99%

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Sustainable Mechanosynthesis of Biologically Active Molecules

et al. 2022

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Synthetic mechanochemistry, the use of mechanical force produced by milling, grinding or extruding, as an activation technique, provides access to chemical entities of all kinds. This Review is focused on examples reported so far of known Active Pharmaceutical Ingredients (APIs), and effectively evaluated bioactive molecules, all prepared by mechanosynthesis. Three families of molecules are discussed: heterocyclic compounds, metal complexes and peptides. Advantages of the mechanochemistry approach are highlighted especially from a green chemistry and efficacy point of view.

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Section: Discussionmentioning

confidence: 99%

“…The compounds were obtained in short reaction time (1 h) and yields ranging from 58 to 92 % (Scheme 3). In this approach, only potassium tert ‐butoxide is necessary to promote the reaction, thus circumventing the use of classical toxic and dangerous coupling reagents at this stage [33] …”

Section: Mechanosynthesis Of Biologically Active Heterocyclic Compoundsmentioning

confidence: 99%

Sustainable Mechanosynthesis of Biologically Active Molecules

et al. 2022

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“…In a previous study, we successfully used a ball mill to synthesize a broad range of glycosylamines and glycamines from free sugars [36,37]. Furthermore, a very recent article dealing with the direct amidation of esters in a ball mill highlighted (during the course of our study) the requirement for more eco-friendly approaches for the synthesis of amide groups [38].…”

Section: Introductionmentioning

confidence: 95%

Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones

Bil

Abdellahi

Pourceau

et al. 2022

Sustainable Chemistry

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Sugar amides, such as aldonamides, are interesting, sugar-based molecules used in various fields, from detergency to medicine. Nevertheless, their valorization, especially as alternatives to petroleum-based substances, can be slowed down by their synthetic pathway, which is generally not in accordance with green chemistry principles, and is also not economically competitive. We propose herein a fast procedure for the synthesis of aldonamide-derived glycoconjugates with mechanochemistry. The conditions were first optimized with galactonolactone, used as a model lactone, and dodecylamine. After only 5 min of grinding of stoechiometric amounts of amine and lactone, in the presence of water used as a Liquid Assisted Grinding (LAG) agent, the corresponding galactonamide was isolated with a high yield (90%) after a simple aqueous work-up. The optimized conditions were then applied to a wide variety of amines and sugar lactones, showing the versatility of the methodology. Gluco- and ribono-lactone exhibited similarly excellent reactivity, showing that the procedure is not sugar-dependent. Furthermore, the procedure was shown to be compatible with various functional groups such as alkene, alkyne, thiol, ester and hydroxyl.

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“…All of this can be largely achieved in the absence of solvent, and thus the reactor environment of a ball mill is receiving increasing interest in recent times. [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict What We Might Expect?

Williams¹,

Morrill²,

Browne

2021

ChemSusChem

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Ball mills input energy to samples by pulverising the contents of the jar. Each impact on the sample or wall of the jar results in an instantaneous transmission of energy in the form of a temperature and pressure increase (volume reduction). Conversely, enantioselective organocatalytic reactions proceed through perceived delicate and well‐organised transition states. Does there exist a dichotomy in the idea of enantioselective mechanochemical organocatalysis? This Review provides a survey of the literature reporting the combination of organocatalytic reactions with mechanochemical ball milling conditions. Where possible, direct comparisons of stirred in solution, stirred neat and ball milled processes are drawn with a particular focus on control of stereoselectivity.

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Direct Amidation of Esters by Ball Milling**

Cited by 67 publications

References 124 publications

Sustainable Mechanosynthesis of Biologically Active Molecules

Sustainable Mechanosynthesis of Biologically Active Molecules

Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones

Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict What We Might Expect?

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