- Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates
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An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.
- Li, Bin,Shen, Nana,Yang, Yujie,Zhang, Xinying,Fan, Xuesen
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supporting information
p. 388 - 393
(2021/01/13)
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- Gold-Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne-Tethered Diazo Compounds with Benzo[c]isoxazoles for the Assembly of 4-Iminonaphthalenones and Indenes
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A gold-catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4-iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6-endo-di
- Bao, Ming,Xie, Xiongda,Hu, Wenhao,Xu, Xinfang
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supporting information
p. 4018 - 4023
(2021/07/10)
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- Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives
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An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.
- Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Shang, Yongjia
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supporting information
p. 3890 - 3894
(2020/05/18)
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- Silver-catalyzed regioselective synthesis of acridines, quinolines, and naphthalenes from 3-(2-alkynyl)aryl-β-ketoesters
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A facile, efficient, and general synthetic method for a wide range of medicinally useful 2-carboxylate derivatives of acridinols, quinolinols, and naphthalenols has been developed via silver-catalyzed electrophilic cyclization of 3-(2-alkynyl)aryl-β-ketoesters. The designed reaction involved selective C-C bond formation on more electrophilic alkynyl carbon, which resulted in the regioselective 6-endo-dig cyclized product, as confirmed by X-ray crystallographic studies. The deuterium labeling experiments were performed to support the proposed mechanism. The synthetic methodology accommodates wide functional group variations on alkyne, which proves to be highly advantageous for structural and biological activity assessments.
- Shukla, Satya Prakash,Tiwari, Rakesh,Verma, Akhilesh Kumar
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p. 9035 - 9044
(2012/10/30)
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- Alternatives to α-Diazo Ketones for Tandem Cyclization-Cycloaddition and Carbenoid-Alkyne Metathesis Strategies. Novel Cyclic Enol-Ether Formation via Carbonyl Ylide Rearrangement Reactions
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Attempts to form carbonyl ylides from free carbenes derived from diazirines or diazo compounds lacking electron-withdrawing substituents resulted in azine formation or Wolff rearrangement, respectively.Iodonium ylides proved to be a possible alternative to α-diazo compounds for metallocarbenoid generation, similar reactivity being observed for both systems.Studies into the rearrangement chemistry of carbonyl ylides provided a novel cyclic enol-ether synthesis via a 1,4-hydrogen shift process.
- Fairfax, David J.,Austin, David J.,Xu, Simon L.,Padwa, Albert
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p. 2837 - 2844
(2007/10/02)
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