Synthesis of (<i>E</i>)‐α,β‐Unsaturated Carbonyls <i>via</i> Silver‐Catalyzed Tandem Epoxide Rearrangement/Intermolecular Carbonyl‐ Heteroalkyne Metathesis

Zhu, Hai‐Liang; Jin, Weiwei; He, Jiayao; Zhang, Yan; Zhu, Gangguo

doi:10.1002/adsc.201600623

Cited by 15 publications

(1 citation statement)

References 56 publications

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“…This compound is known, and the spectroscopic data match those reported. 21 1 H NMR (300 MHz, CDCl 3 ) δ = 7.36−7.31 (m, 1H), 7.20−7.15 (m, 1H), 7.15−7.06 (m, 2H), 4.24 (q, J = 7.1 Hz, 2H), 2.41 (s, 3H), 1.48 (t, J = 7. 1 Hz,3H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers

et al. 2023

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Enol esters and conjugated enynes are valuable structural motifs for synthetic chemistry and material sciences. Herein, the synthesis of tetra-substituted enol ester 2-iodobenzoate derivatives was achieved in good yields at room temperature through a gold-catalyzed acyloxyalkynylation of sensitive ynol ethers with ethynylbenziodoxolones (EBXs), the latter acting as bifunctional reactants. The conversion is highly regioselective with a broad substrate scope. Mechanistically, an Au(III) species is the key intermediate of an Au(I)/Au(III) redox cycle. The reaction is synthetically useful and can easily be scaled up to gram scale.

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Section: ■ Conclusionmentioning

confidence: 99%

Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers

et al. 2023

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Lewis Acid‐Catalyzed Yne‐Carbonyl Metathesis of Ynamides and Cyclobutanones: Facile Synthesis of Functionalized Alkylidenecyclobutanes

et al. 2018

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An atom‐economical strategy for the synthesis of functionalized alkylidenecyclobutanes (ACBs) via Lewis acid‐catalyzed yne‐carbonyl metathesis of ynamides and cyclobutanones is described. This strategy features mild reaction conditions, ready availability of starting materials, and broad functional group tolerability. Furthermore, the imide group is easily converted to acid, ester, and amide, thus providing an efficient access to various functionalized ACBs.

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Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

Rao¹,

Sudheer²,

Battula³

2022

ChemistrySelect

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A facile triflic acid catalyzed method to synthesize 1-arylnaphthalenes from one-pot annulation reaction of arylepoxides and arylalkynes has been reported. The annulation reaction involves a successive epoxide to carbonyl rearrangement, electrophilic attack of carbonyl on arylalkyne followed by cyclization catalyzed by triflic acid. The present catalyst effects this transformation at room temperature itself.

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Synthesis of (E)‐α,β‐Unsaturated Carbonyls via Silver‐Catalyzed Tandem Epoxide Rearrangement/Intermolecular Carbonyl‐ Heteroalkyne Metathesis

Cited by 15 publications

References 56 publications

Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers

Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers

Lewis Acid‐Catalyzed Yne‐Carbonyl Metathesis of Ynamides and Cyclobutanones: Facile Synthesis of Functionalized Alkylidenecyclobutanes

Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

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