Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C<sub>60</sub> by Using a Flow Reaction System

Ueda, Mitsuhiro; Hayama, Miho; Hashishita, Hiroyuki; Munechika, Aiko; Fukuyama, Takahide

doi:10.1002/ejoc.201901072

Cited by 4 publications

(3 citation statements)

References 41 publications

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“…Ueda and co-workers presented the synthesis of cyclopentene/cyclobutane-annulated fullerenes via base-catalyzed [3+2] and [2+2] cycloaddition of 1,3-bifunctional allenes (generated in situ) in ortho -dichlorobenzene (ODCB) [ 80 ]. The synthesis of cyclopentene-annulated fullerenes was obtained from Et 3 N-catalyzed [3+2] cycloaddition of propiolic acid esters and 1,2-diaryl-1,2-diketones with C 60 .…”

Section: Review Of Literaturementioning

confidence: 99%

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

et al. 2023

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Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp2 hybridized carbon atoms. The chemistry of allenes has been well documented over the last decades. They are more reactive than alkenes due to higher strain and exhibit significant axial chirality, thus playing a vital role in asymmetric synthesis. Over a variety of organic transformations, allenes specifically undergo classical metal catalyzed cycloaddition reactions to obtain chemo-, regio- and stereoselective cycloadducts. This review briefly describes different types of annulations including [2+2], [2+2+1], [3+2], [2+2+2], [4+2], [5+2], [6+2] cycloadditions using titanium, cobalt, rhodium, nickel, palladium, platinum, gold and phosphine catalyzed reactions along with a mechanistic study of some highlighted protocols. The synthetic applications of these reactions towards the synthesis of natural products such as aristeromycin, ent-[3]-ladderanol, waihoensene(−)-vindoline and (+)-4-epi-vindoline have also been described.

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Section: Review Of Literaturementioning

confidence: 99%

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

et al. 2023

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“…Other continuous-flow systems in which a ketene was generated in situ and then directed into a [2 + 2] cycloaddition have been reported, many of these reactions present improved results compared to their batch modes with higher throughputs [ 522 – 523 ].…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…[5] The [2 + 2] cycloaddition between in situ-generated 1,3bifunctional allenes and C 60 was carried out by using a continuous flow packed-bed reactor and silica-supported tertiary amine. [77] Cyclobutenones were identified as secondary products when forming ketenes in flow and reacting them to form amides and esters. Without adding alcohols or amines, the cycloadduct was obtained with 95 % yield in 10 min at 180 °C.…”

Section: Non-photochemical [2 + 2] Cycloaddition To Carbocyclesmentioning

confidence: 99%

Flow Chemistry for Cycloaddition Reactions

2020

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Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo-and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2 + 2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.

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Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C₆₀ by Using a Flow Reaction System

Cited by 4 publications

References 41 publications

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Flow Chemistry for Cycloaddition Reactions

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Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C60 by Using a Flow Reaction System

Cited by 4 publications

References 41 publications

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Flow Chemistry for Cycloaddition Reactions

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Controlled [3+2] and [2+2] Cycloadditions of 1,3‐Bifunctional Allenes with C₆₀ by Using a Flow Reaction System