Bi(III)-Catalyzed Intermolecular Reactions of (<i>Z</i>)-Pent-2-en-4-yl Acetates with Ethynylarenes for the Construction of Multisubstituted Fluorene Skeletons through a Cascade Electrophilic Addition/Cycloisomerization Sequence

Wang, Xiang-Chuan; Yan, Rulong; Zhong, Mei‐Jin; Liang, Yong‐Min

doi:10.1021/jo202607z

Cited by 31 publications

(6 citation statements)

References 48 publications

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“…( Z )-Pent-2-en-4-yl acetates react with ethynylarenes (MeNO 2 , 80 °C, 6–12 h) in the presence of Bi(III) (BiBr 3 10 mol %, 2,2′-bipyridine 20 mol %) to obtain substituted fluorenes (18 examples, 51–82%) …”

Section: Reactions Catalyzed By Other Metalsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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This review is focused on the analysis of current data on new methods of alkenylation of arenes and heteroarenes with alkynes by transition metal catalyzed reactions, Bronsted/Lewis acid promoted transformations, and others. The synthetic potential, scope, limitations, and mechanistic problems of the alkenylation reactions are discussed. The insertion of an alkenyl group into aromatic and heteroaromatic rings by inter- or intramolecular ways provides a synthetic route to derivatives of styrene, stilbene, chalcone, cinnamic acid, various fused carbo- and heterocycles, etc.

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Section: Reactions Catalyzed By Other Metalsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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“…A recent Bi III ‐catalyzed synthesis of multisubstituted fluorenes was reported by Liang and co‐workers, who found that the reaction of ( Z )‐pent‐2‐en‐4‐yl acetates 50 with ethynylarenes 51 in the presence of BiBr 3 (10 mol %) and 2,2′‐bipyridine (20 mol %) in CH 3 NO 2 afforded fluorene derivatives 52 in moderate to good yields (Scheme ) 37. Based on the experimental observations, a mechanistic rationale was proposed (Scheme ).…”

Section: Other Transition Metal‐catalyzed Syntheses Of Fluorenesmentioning

confidence: 99%

Recent Progress towards Transition‐Metal‐Catalyzed Synthesis of Fluorenes

Zhou

Pan

Zhu

et al. 2015

Chemistry A European J

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Fluorenes are a commonly encountered structural motif in materials science, pharmaceutical chemistry, and organic synthesis. Among various strategies towards the synthesis of this unique structure, transition metal-catalyzed functionalization has emerged as one of the most efficient methods. This Minireview presents an overview of the recent advances in this emerging area by highlighting the reactions' specificity and applicability and, where possible, provides a mechanistic rationale.

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“…The scope of the cyclization towards the various fluorenes and fluorenols was investigated and the reaction proved to be general for various substrates. For other methods of synthesis of the fluorene core, see the references [16–19] . We noticed an instability of some synthesized products which upon standing changed color to purple/red.…”

Section: Introductionmentioning

confidence: 87%

The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals

Nallappan,

Lapinskaite,

Hájíček

et al. 2023

ChemPlusChem

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We report a biomimetic synthesis of polyarylated fluorene derivatives. The molecules are formed via intramolecular electrophilic aromatic substitution, resembling a cyclization leading towards the natural selaginpulvilins from selaginellins. The scope of the reaction was investigated, and the products were obtained in 60‐95% yields. Some of the compounds decompose to a stable radical. We investigated the nature and the origin of the radical using experimental methods, including EPR or electrochemical measurements, as well as theoretical methods, such as DFT calculations. Based on our observations, we hypothesize, that phenoxy radicals are formed in the first instance, which however undergo internal rearrangement to thermodynamically more stable carbon‐centered radicals. The preliminary data also show the cytotoxic properties of some of the molecules.

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Bi(III)-Catalyzed Intermolecular Reactions of (Z)-Pent-2-en-4-yl Acetates with Ethynylarenes for the Construction of Multisubstituted Fluorene Skeletons through a Cascade Electrophilic Addition/Cycloisomerization Sequence

Cited by 31 publications

References 48 publications

Alkenylation of Arenes and Heteroarenes with Alkynes

Alkenylation of Arenes and Heteroarenes with Alkynes

Recent Progress towards Transition‐Metal‐Catalyzed Synthesis of Fluorenes

The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals

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