Mechanochemical Syntheses of <i>N</i>-Containing Heterocycles with TosMIC

Schumacher, Christian; Molitor, Claude; Smid, Sabrina; Truong, Khai‐Nghi; Bolm, Carsten

doi:10.1021/acs.joc.1c01529

Cited by 19 publications

(4 citation statements)

References 131 publications

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“…Another synthetical and environmentally friendly approach is the mechanochemical one, used for the van Leusen pyrrole synthesis with base catalysts. The process leads to 3,4‐disubstitued pyrroles 268 in moderate to excellent yields (Scheme 65) [106] The developed protocol established the reaction between toluenesulfonylmethyl isocyanide 266 and chalcone 267 in the presence of a base. The reactants were milled in the presence of three balls (7 mm in ø) for 90 min at 30 Hz.…”

Section: Innovative “Green” Synthesismentioning

confidence: 99%

From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

Rizzo,

Pace,

Pibiri

et al. 2024

ChemSusChem

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Synthesis of heterocyclic compounds is fundamental for all the research area in chemistry, from drug synthesis to material science. In this framework, catalysed synthetic methods are of great interest to effective reach such important building blocks. In this review, we will report on some selected examples from the last five years, of the major improvement in the field, focusing on the most important conventional catalytic systems, such as transition metals, organocatalysts, to more sustainable ones such as photocatalysts, iodine‐catalysed reaction, electrochemical reactions and green innovative methods.

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Section: Innovative “Green” Synthesismentioning

confidence: 99%

From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

Rizzo,

Pace,

Pibiri

et al. 2024

ChemSusChem

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“…Another ball-milling approach for the synthesis of 3,4-disubstituted pyrroles has been accomplished by Bolm et al [37] in 2021 (Figure 2). Under the influences of organic base DBU (1,.0]undec-7-ene), the desired products 9 derived from the reaction of enones 8 with TosMIC (toluenesulfonylmethyl isocyanide) 7 at milling frequency of 35 Hz for 1 hour in solvent-free condition has been obtained in moderate to good yield (34-92% yield).…”

Section: Synthesis Of Pyrrolesmentioning

confidence: 99%

Mechanochemistry in Organocatalysis: A Green and Sustainable Route toward the Synthesis of Bioactive Heterocycles

Borah¹,

Chowhan²

2022

Green Chemistry - New Perspectives

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Considering the great prevalence of heterocyclic compounds in the core structure of numerous natural products, synthetic drug candidates, active pharmaceutical ingredients, and also in optoelectronic materials; tremendous efforts have been dedicated toward their synthesis and functionalization. But, the exploitation of hazardous, volatile organic solvents and toxic reagents caused disadvantageous effects on the atom economy and eco-friendly nature of the chemical transformation. Therefore, developing chemical processes providing easy access to complex target molecules by avoiding the utilization of hazardous solvents and reagents for making our environment toxic-free is of increasing significance for chemists in both academia and industry. The synergic combination of the features of mechanochemical activation as alternative energy input with the efficiency associated with small organic molecules that can catalyze chemical reactions is predominantly relevant to fulfill the goal of green and sustainable chemistry. This chapter is dedicated to providing a critical overview on the application of mechanochemical techniques for the synthesis of five- and six-membered heterocycles, as well as complex-fused heterocycles and spiro-heterocycles under organocatalytic conditions.

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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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Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

Cited by 19 publications

References 131 publications

From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

Mechanochemistry in Organocatalysis: A Green and Sustainable Route toward the Synthesis of Bioactive Heterocycles

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

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