Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination

Howard, Joseph L.; Sagatov, Yerbol; Repusseau, Laura; Schotten, Christiane; Browne, Duncan L.

doi:10.1039/c6gc03139k

Cited by 112 publications

(88 citation statements)

References 44 publications

(5 reference statements)

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“…Stoichiometric selectivity in organic mechanosynthesis of: a) thioureas; [87] b) salicylaldimines; [88] c) fluorinated b-diketones. [89] Angewandte Chemie carboxylic and boronic acids using H 2 17 O, [94] while Lukin et al demonstrated rapid deuteration with D 2 O. [95]…”

Section: Benefits Of Solvent-free Environmentmentioning

confidence: 99%

Mechanochemistry for Synthesis

2019

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Mechanochemical solvent‐free reactions by milling, grinding or other types of mechanical action have emerged as a viable alternative to solution chemistry. Mechanochemistry offers not only a possibility to eliminate the need for bulk solvent use, and reduce the generation of waste, but it also unlocks the door to a different reaction environment in which synthetic strategies, reactions and molecules previously not accessible in solution, can be achieved. This Minireview examines the potential of mechanochemistry in chemical and materials synthesis, by providing a cross‐section of the recent developments in using ball milling for the formation of molecules and materials based on covalent and coordination bonds.

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Section: Benefits Of Solvent-free Environmentmentioning

confidence: 99%

Mechanochemistry for Synthesis

2019

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“…It was found that many reactions occur much faster as in solution, they can be performed under milder conditions, and the product is isolated in higher yields, compared to the corresponding reaction in solution. [17] Similar process improvements under mechanochemical conditions were achieved for a variety of reactions, for example the amidation of aldehydes, [18] the fluorination of 1,3-diketones, [19] the Michael addition, [20,21] the Knoevenagel condensation, [22] and the Morita-Baylis-Hillman reaction. The reactions were over in 4 h, yielding the products in very good to excellent yield (76-95 %).…”

Section: Mechanochemistry In Organic Synthesismentioning

confidence: 75%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

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Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

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“…In 2016, Browne and co-workers reported selective mechanochemical fluorination of 1,3-dicarbonyl compounds using selectfluor [ 101 – 102 ]. They could control the selectivity of the reaction through LAG using ACN (≈10% v/v of total materials) to get predominantly mono-fluorinated product over difluorinated derivatives ( Scheme 27 ).…”

Section: Reviewmentioning

confidence: 99%

Mechanochemical synthesis of small organic molecules

Achar

Bose

Mal

2017

Beilstein J. Org. Chem.

230

111

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With the growing interest in renewable energy and global warming, it is important to minimize the usage of hazardous chemicals in both academic and industrial research, elimination of waste, and possibly recycle them to obtain better results in greener fashion. The studies under the area of mechanochemistry which cover the grinding chemistry to ball milling, sonication, etc. are certainly of interest to the researchers working on the development of green methodologies. In this review, a collection of examples on recent developments in organic bond formation reactions like carbon–carbon (C–C), carbon–nitrogen (C–N), carbon–oxygen (C–O), carbon–halogen (C–X), etc. is documented. Mechanochemical syntheses of heterocyclic rings, multicomponent reactions and organometallic molecules including their catalytic applications are also highlighted.

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Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination

Abstract: We have identified an example of a mechanochemically milled organic reaction where liquid-assisted grinding controls the selectivity, such a phenomenon has not been reported/observed before.

Cited by 112 publications

References 44 publications

Mechanochemistry for Synthesis

Mechanochemistry for Synthesis

Organic Synthesis without Conventional Solvents

Mechanochemical synthesis of small organic molecules

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