Direct Synthesis of α‐Allenols from TMS‐Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

Huang, Xiaojun; Bugarin, Alejandro

doi:10.1002/chem.201603250

Cited by 10 publications

(6 citation statements)

References 71 publications

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“…Reaction with phosphonium ylide generated from (methoxymethyl)triphenylphosphonium chloride yielded methyl enol ether, which after subsequent heating with diluted sulfuric acid was transformed into 1-indanecarbaldehyde. 23 The next steps were analogous to those of a well-established synthetic protocol. 24 1-Indanecarbaldehyde was alkylated with 3-chloro-2-methyl-1-propene under phase-transfer catalysis conditions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Inhibition of the Decomposition Pathways of Ruthenium Olefin Metathesis Catalysts: Development of Highly Efficient Catalysts for Ethenolysis

Gawin,

Tracz,

Krajczy

et al. 2023

J. Am. Chem. Soc.

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Ruthenium-based Hoveyda-type olefin metathesis catalysts bearing novel rigid spirocyclic alkyl amino carbenes (CAACs) have been developed. They are characterized by exceptional stability toward decomposition through β-elimination and bimolecular pathways, thus enabling unprecedented efficiency in the cross-metathesis of seed oil-derived fatty acid esters with ethylene (ethenolysis). Catalyst loading as low as 100 ppb was applied to the ethenolysis of the model substrate methyl oleate, leading to a remarkable turnover number (TON) of 2.6 million, significantly higher than previously reported (TON 340 000 at 1 ppm and 744 000 at 0.5 ppm catalyst loading). Ethenolysis of methyl esters derived from high oleic sunflower oil and rapeseed oil, readily available on an industrial scale, inexpensive, and renewable feedstocks, was for the first time effectively carried out with 0.5 ppm catalyst loading with TON as high as 964 000.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Inhibition of the Decomposition Pathways of Ruthenium Olefin Metathesis Catalysts: Development of Highly Efficient Catalysts for Ethenolysis

Gawin,

Tracz,

Krajczy

et al. 2023

J. Am. Chem. Soc.

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“…Unless otherwise stated, all reactions were carried out under dry argon. Substrates 1a – 1aa , 1ab , 1ac , 1ad , 1ae – 1ai , 2c – 2d , 2e , and 2h were prepared according to the known reference. Other reagents were obtained from commercial suppliers and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides

et al. 2020

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The first facile and efficient acid-catalyzed direct coupling of a wide range of unprotected 2,3-allenols with arylphosphine oxides was developed, offering a general, one-step approach for the synthesis of structurally diverse γ-ketophosphine oxides accompanied by concurrent CP/CO bond formation with remarkable functional group tolerance and complete atomeconomy under metal-and additive-free conditions. Mechanistic studies showed that this transformation involved a rearrangement and a phospha-Michael reaction.

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“…The authors have cited additional references within the Supporting Information. [57][58][59][60][61][62][63][64][65][66][67]…”

Section: Supporting Informationmentioning

confidence: 99%

On‐Surface Synthesis and Determination of the Open‐Shell Singlet Ground State of Tridecacene**

Zuzak,

Kumar,

Stoica

et al. 2024

Angew Chem Int Ed

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The character of the electronic structure of acenes has been the subject of longstanding discussion. However, convincing experimental evidence of their open‐shell character has so far been missing. Here, we present the on‐surface synthesis of tridecacene molecule by thermal annealing of octahydrotridecacene on Au(111) surface. We characterized the electronic structure of the tridecacene by scanning probe microscopy, which reveals the presence of the inelastic signal at 126 meV. We attribute the inelastic signal to the spin excitation from the singlet diradical ground state to the triplet excited state. To rationalize the experimental findings, we carry out many‐body ab‐initio calculations as well as model Hamiltonian to take into account the effect of metallic substrate. Moreover, we provide a detailed analysis of how the dynamical electron correlation and virtual charge fluctuation between molecule and metallic surface reduces the singlet‐triplet band gap. Therefore, this work provides the first experimental confirmation of the magnetic character of tridecacene.

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Direct Synthesis of α‐Allenols from TMS‐Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

Cited by 10 publications

References 71 publications

Inhibition of the Decomposition Pathways of Ruthenium Olefin Metathesis Catalysts: Development of Highly Efficient Catalysts for Ethenolysis

Inhibition of the Decomposition Pathways of Ruthenium Olefin Metathesis Catalysts: Development of Highly Efficient Catalysts for Ethenolysis

TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides

On‐Surface Synthesis and Determination of the Open‐Shell Singlet Ground State of Tridecacene**

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