Synthesis of 2,3-diarylfluorenones by domino ‘twofold Heck/electrocyclization/dehydrogenation’ reactions of 2,3-dibromoindenone

Akrawi, Omer A.; Khan, Afsar; Hussain, Munawar; Mohammed, Hamid H.; Villinger, Alexander; Langer, Peter

doi:10.1016/j.tetlet.2013.03.011

Cited by 11 publications

(9 citation statements)

References 36 publications

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“…The optimized conditions were 2-bromobenzaldehyde (49), with 1.1 equiv. phenylboronic acid (48) in the presence of 3 mol % catalyst, 6 equiv. K 2 CO 3 , and 1.5 mL toluene at 55°C for 5 h. Further, add 1.5 mL DMA at 120°C for 10 h (Scheme 9).…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…The one-pot cascade reaction takes place between ortho methyl ketoxime (62) and phenylboronic acid (48) in the presence of 10 mol % of Pd(OAc) 2 , 2.5 equiv. Cu(OTf) 2 , 3 Å MS in dioxane at 90°C for 24 h. There after the cyclization takes place in the presence of 2.0 equiv.…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…[37] Ortho cyclopalladation takes place in o-methyl oxime 62, leading to 64. 65 is generated by transmetalation with phenylboronic acid (48), which further undergoes reductive elimination to form 66. By the addition of TfOH, 67 is formed, which further undergoes hydrolysis in the presence of acid to form the desired product 63 (Scheme 15).…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…O-bromoiodobenzene (88) treated with 1.2 equiv. of phenylboronic acid (48) in the presence of 5 mol % Pd(OAc) 2 , 3.0 equiv. Cs 2 CO 3 ,1.0 equiv.…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…triethylamine in DMF at 65°C for 5 h afforded 95 % yields of fluorenone (Scheme 30). [48] The respective yields in case of domino Double Heck reaction is dependent on the reaction conditions like the type of catalysts, solvents, bases, and ligands. In the presence of ligands like P(Cy) 3 , X-phos, or Sphos lesser yields were obtained.…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

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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: 99%

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…O-bromoiodobenzene (88) treated with 1.2 equiv. of phenylboronic acid (48) in the presence of 5 mol % Pd(OAc) 2 , 3.0 equiv. Cs 2 CO 3 ,1.0 equiv.…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

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A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

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Beyond the Corey–Chaykovsky Reaction: Synthesis of Unusual Cyclopropanoids via Desymmetrization and Thereof

Patel

Mishra

Mukhopadhyay

et al. 2019

Chemistry An Asian Journal

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Desymmetrization-based protocols for the synthesis of highly functionalized indeno-spirocyclopropanes and cyclopropa-fused indanes have been established through unexpectedr eactions triggered by the Corey-Chaykovsky reagent. These structures were further elaborated in one step to privileged scaffolds such as fluorenones, indenones, and naphthaphenones. For instance, an acid-catalyzedt ransformation of indeno-spirocyclopropanes provided fluorenones via ah omo-Nazarov-type cyclization, and naphthaphenones were obtained via an acidcatalyzed cyclopropane ring-opening/retro-Michael sequence.Cyclopropanes are important structural units presenti ns everal bioactive natural productsa nd pharmaceutically relevant compounds including af ew marketed drugs (Figure 1). [1] Medicinal chemists take advantage of the enhanced metabolic stability and conformational rigidity offered by cyclopropanes during drug design and development. [2] In addition, the strained Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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