Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction

Manick, Anne‐Doriane; Salgues, Bruno; Parrain, Jean‐Luc; Zaborova, Elena; Fagès, Frédéric; Amatore, Muriel; Comméiras, Laurent

doi:10.1021/acs.orglett.0c00235

Cited by 15 publications

(16 citation statements)

References 37 publications

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“…[52] Commeiras . [53] The yield was also dependent on the reaction conditions, whereas decreasing temperature led to lower yields (at 50°C and room temperature yields were 29 % and 28 % respectively).…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 96%

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

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Fluorenones are important constituents in material, medical and chemical sciences with potential applications in various domains. The key factors responsible for the diverse usage of fluorenones in material sciences are their intriguing and tunable photo, as well as physico‐chemical properties. Besides this, the presence of conjugated poly‐(en)ynes in the fluorenones makes them molecules of interest in material sciences. Fluorenones show various biological activities like antibiotics, anticancer, antiviral, and neuromodulatory, etc. Organic chemists are developing various protocols for the synthesis of fluorenones. Despite several protocols developed for their synthesis since 1931, there is no review covering their entire synthetic protocols. This review includes several classical and novel synthetic approaches for the synthesis of fluorenones. Furthermore, we delineated the mechanism by which they have been synthesized.

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Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 96%

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

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“…In 2020, Amatore, Commeiras, and co-workers reported the Rh-catalyzed [2+2+2] cycloaddition reaction of 1,6diynes with 3-acetoxy or-3-alkoxyindenones as surrogates of the highly reactive benzocyclopentynone 2 partner, in the presence of 10 mol% [Rh(C 6 H 10 )Cl] 2 and racemic BINAP combined with AgBF 4 and CaH 2 as a hydride source additive at 80 °C in anhydrous 1,2-dichloroethane for 12 h to provide the desired substituted fluorenones in 36-81% yield (Scheme 29). 91 Optimization of the reaction indicated that cycloaddition carried out in the presence of AgSbF 6 or AgOTf led to side reactions. Variable yields were obtained with diynes bearing different tethers (up to 81% with a gem-dicyanomethylene tether).…”

Section: Scheme 28mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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“…Similarly, Amatore and co‐workers designed a straightforward methodology for the preparation of substituted fluorenones 81 from diynes 79 and 3‐alkoxy, 3‐acetoxyindenones 80 via [2+2+2] cycloaddition reaction using Rh‐catalyst (Scheme 29). [48] The formation of fluorenone through the oxidative coupling of 79 with Rh‐catalyst to give rhodacyclopentadiene intermediate. Then undergoes rearomatization after reductive elimination, which affords the corresponding fluorenone 81 .…”

Section: Reactions Of Alkyl Enol Ethersmentioning

confidence: 99%

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

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Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond‐forming reactions include metal‐catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge.

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Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction

Cited by 15 publications

References 37 publications

A Perspective on Synthesis and Applications of Fluorenones

A Perspective on Synthesis and Applications of Fluorenones

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

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