Light-induced iodoperfluoroalkylation reactions of carbon–carbon multiple bonds in water

Slodowicz, Mariel Pamela; Barata‐Vallejo, Sebastián; Vázquez, Alvaro J.; Nudelman, Norma Sbarbati; Postigo, Al

doi:10.1016/j.jfluchem.2011.10.002

Cited by 39 publications

(18 citation statements)

References 54 publications

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“…However, using ESI-MS, negative mode, with an ionization potential of 60 eV, the signal for the molecular ion could be detected. Spectroscopical data of compound 13, 25,32 is consistent with previously published data for this compound.…”

Section: Methodssupporting

confidence: 89%

Perfluoroalkylation of alkenes and alkynes in water

Vázquez¹,

Nudelman²

2015

Arkivoc

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Perfluoroalkylation of alkenes and alkynes was performed using thermal initiation by ACCN (1,1'-azobis(cyclohexanecarbonitrile)) in water, with good yields. The procedure is simple and more ecofriendly that most of the methods published for the synthesis of related compounds. Using water (without any cosolvent or metal catalysts), it allows the synthesis of the addition products with medium to high yields.

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Section: Methodssupporting

confidence: 89%

Perfluoroalkylation of alkenes and alkynes in water

Vázquez¹,

Nudelman²

2015

Arkivoc

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“…We also examined alkynes in this reaction (Table ). Various alkyl‐substituted alkynes were applicable to the reaction, and the ( E ) stereoisomers were obtained as the major isomers in large amounts . Additionally, the reaction was effective for different perfluoroalkyl iodides (including difluoroacetate).…”

Section: Resultsmentioning

confidence: 99%

Metal‐Free Visible‐Light Radical Iodoperfluoroalkylation of Terminal Alkenes and Alkynes

Yajima

Ikegami

2017

Eur J Org Chem

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“…Also, carbon-halogen bond was occasionally cleaved by harsh UV light to initiate the catalytic reaction. [15,16] Subsequently, lots of metal-mediated catalysts, such as Cu, [17] Ni, [18,19] Ru, [20,21] Pd [22] and Fe [23] catalysts were used as radical initiators in ATRA process, showing a high reaction efficiency. In this regard, the metal can trigger generation of free radicals, while formed metal-halide complex can achieve rapid transfer of the halide from the metal to the carbon-centered radical.…”

Section: Introductionmentioning

confidence: 99%

Reaction Mechanism and Kinetics study on Addition of CCl₄ to 1‐hexene Catalyzed by Mo‐Mo Quintuply‐bond

Kang

Huo

Meng

et al. 2020

Applied Organom Chemis

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Transition metal-catalyzed atom transfer radical addition (ATRA) reactions are an effective and versatile strategy for constructing carbon-carbon bonds in organic synthesis. Typically, the metal center in this metal-assisted radical transformation undergoes a reversible redox process. In this work, a quintuply-bonded dinuclear complex, Mo 2 (N^N) 2 {N^N = μ-κ 2-CH[N(2,6-iPr 2 C 6 H 3)] 2 }, has been investigated as potential catalyst for radical addition of CCl 4 to 1-hexene by performing density functional theory (DFT) calculations. The study shows that the Mo 2 (N^N) 2-mediated radical addition reaction is computationally predicted to occur with acceptable activation energies, indicating that the Mo-Mo quintuple bond can be applied as an effective catalyst for this transformation under mild conditions. The whole reaction involves 3 steps, two of which are metal-mediated. Firstly, the C-Cl bond activiation catalyzed by Mo 2 (N^N) 2 to obtain Mo 2 (N^N) 2 Cl and •CCl 3 radical; Then the •CCl 3 radical interacts with 1-hexene to get an addition, the addition product reacts with the Mo 2 (N^N) 2 Cl to get the last product and regenerate the catalyst Mo 2 (N^N) 2. Both the thermodynamic and kinetic study show that the second step is the rate-determine step. When coordinating solvent pyridine is added to the catalytic reaction, the reaction is suppressed due to their high energies barriers, which is consistent with experimental results.

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Light-induced iodoperfluoroalkylation reactions of carbon–carbon multiple bonds in water

Cited by 39 publications

References 54 publications

Perfluoroalkylation of alkenes and alkynes in water

Perfluoroalkylation of alkenes and alkynes in water

Metal‐Free Visible‐Light Radical Iodoperfluoroalkylation of Terminal Alkenes and Alkynes

Reaction Mechanism and Kinetics study on Addition of CCl₄ to 1‐hexene Catalyzed by Mo‐Mo Quintuply‐bond

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Light-induced iodoperfluoroalkylation reactions of carbon–carbon multiple bonds in water

Cited by 39 publications

References 54 publications

Perfluoroalkylation of alkenes and alkynes in water

Perfluoroalkylation of alkenes and alkynes in water

Metal‐Free Visible‐Light Radical Iodoperfluoroalkylation of Terminal Alkenes and Alkynes

Reaction Mechanism and Kinetics study on Addition of CCl4 to 1‐hexene Catalyzed by Mo‐Mo Quintuply‐bond

Contact Info

Product

Resources

About

Reaction Mechanism and Kinetics study on Addition of CCl₄ to 1‐hexene Catalyzed by Mo‐Mo Quintuply‐bond