Mechanosynthesis of Odd‐Numbered Tetraaryl[<i>n</i>]cumulenes

Ardila‐Fierro, Karen J.; Bolm, Carsten; Hernández, José G.

doi:10.1002/ange.201905670

Cited by 19 publications

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“…Following this line of research, Bolm et al have recently established an efficient two-stage procedure for the synthesis of tetraaryl[ n ]cumulenes ( n = 3, 5) based on the mechanochemical activation of ketones, calcium carbide, and potassium hydroxide via an initial Favorskii alkynylation-type reaction in a ball mill (Schemes and ).…”

Section: Mechanochemistry For Classical C–c Bond-forming Reactionsmentioning

confidence: 99%

Metal-Mediated and Metal-Catalyzed Reactions Under Mechanochemical Conditions

et al. 2020

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The extraordinary impact of metal-based complexes on synthetic methods is still recognized nowadays, and attempts are currently undertaken to further extend the use of metal-assisted chemistry to environmentally friendly processes within the strongly invoked green chemistry paradigm. In recent years, mechanochemistry seems to provide attractive responses with processing methods having origins lost in the mists of time. Focusing on the panorama of organic synthesis, this Review highlights some recently developed metal-assisted mechanochemical reactions to introduce the reader into the fascinating, quite unexplored world of mechanochemistry.

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Section: Mechanochemistry For Classical C–c Bond-forming Reactionsmentioning

confidence: 99%

Metal-Mediated and Metal-Catalyzed Reactions Under Mechanochemical Conditions

et al. 2020

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The Mechanochemical Synthesis and Activation of Carbon‐Richπ‐Conjugated Materials

et al. 2022

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Dedicated to the 75th birthday of Klaus Müllen.Mechanochemistry uses mechanical force to break, form, and manipulate chemical bonds to achieve functional transformations and syntheses. Over the last years, many innovative applications of mechanochemistry have been developed. Specifically for the synthesis and activation of carbon-rich 𝝅-conjugated materials, mechanochemistry offers reaction pathways that either are inaccessible with other stimuli, such as light and heat, or improve reaction yields, energy consumption, and substrate scope. Therefore, this review summarizes the recent advances in this research field combining the viewpoints of polymer and trituration mechanochemistry. The highlighted mechanochemical transformations include 𝝅-conjugated materials as optical force probes, the force-induced release of small dye molecules, and the mechanochemical synthesis of polyacetylene, carbon allotropes, and other 𝝅-conjugated materials.

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Mechanochemical Synthesis of Corannulene‐Based Curved Nanographenes

et al. 2020

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It is shown that corannulene-based strained psurfaces can be obtained through the use of mechanochemical Suzuki and Scholl reactions.B esides being solvent-free,t he mechanochemical synthesis is high-yielding,fast, and scalable. Therefore,gram-scale preparation can be carried out in afacile and sustainable manner.The synthesized nanographene structure carries positive (bowl-like) and negative (saddle-like) Gaussian curvatures and adopts an overall quasi-monkey saddle-type of geometry.Interms of properties,the non-planar surface exhibits ah igh electron affinity that was measured by cyclic voltammetry,w ith electrolysis and in situ UV/vis spectroscopye xperiments indicating that the one-electron reduced state displays al ong lifetime in solution. Overall, these results indicate the future potential of mechanochemistry in accessing synthetically challenging and functional curved p-systems. Scheme 1. Synthesis of curved p-systems.

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Mechanosynthesis of Odd‐Numbered Tetraaryl[n]cumulenes

Abstract: Scheme 1. a) Carbyne, polyynes, and cumulenes. b) The most common solution-based approach towards the synthesis of [3]cumulenes.

Cited by 19 publications

References 61 publications

Metal-Mediated and Metal-Catalyzed Reactions Under Mechanochemical Conditions

Metal-Mediated and Metal-Catalyzed Reactions Under Mechanochemical Conditions

The Mechanochemical Synthesis and Activation of Carbon‐Richπ‐Conjugated Materials

Mechanochemical Synthesis of Corannulene‐Based Curved Nanographenes

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