Palladium‐Catalyzed Tandem Cyclization of Bromoenynes through Aromatic CH Bond Functionalization

Ohno, Hiroaki; Yamamoto, Mio; Iuchi, Mutsumi; Tanaka, Tetsuaki

doi:10.1002/anie.200500159

Cited by 54 publications

(14 citation statements)

References 57 publications

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“…Note that φ hc is 1/2 of the total potential drop across the entire cell due to the symmetries of the cell geometry and ion models used here. Using equation (1), the rate at which the half-cell potential drop φ hc changes under a constant-current charging condition is given by…”

Section: Resultsmentioning

confidence: 99%

Dynamics of electrical double layer formation in room-temperature ionic liquids under constant-current charging conditions

Jiang

Huang

Zhao

et al. 2014

J. Phys.: Condens. Matter

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We report detailed simulation results on the formation dynamics of an electrical double layer (EDL) inside an electrochemical cell featuring room-temperature ionic liquids (RTILs) enclosed between two planar electrodes. Under relatively small charging currents, the evolution of cell potential from molecular dynamics (MD) simulations during charging can be suitably predicted by the Landau-Ginzburg-type continuum model proposed recently (Bazant et al 2011 Phys. Rev. Lett. 106 046102). Under very large charging currents, the cell potential from MD simulations shows pronounced oscillation during the initial stage of charging, a feature not captured by the continuum model. Such oscillation originates from the sequential growth of the ionic space charge layers near the electrode surface. This allows the evolution of EDLs in RTILs with time, an atomistic process difficult to visualize experimentally, to be studied by analyzing the cell potential under constant-current charging conditions. While the continuum model cannot predict the potential oscillation under such far-from-equilibrium charging conditions, it can nevertheless qualitatively capture the growth of cell potential during the later stage of charging. Improving the continuum model by introducing frequency-dependent dielectric constant and density-dependent ion diffusion coefficients may help to further extend the applicability of the model. The evolution of ion density profiles is also compared between the MD and the continuum model, showing good agreement.

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Section: Resultsmentioning

confidence: 99%

Dynamics of electrical double layer formation in room-temperature ionic liquids under constant-current charging conditions

Jiang

Huang

Zhao

et al. 2014

J. Phys.: Condens. Matter

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“…www.eurjoc.orgdem bis-cyclization transformation. [69] In particular, when enantiomerically pure 78 was treated with Pd(OAc) 2 (5 %) and Cs 2 CO 3 in EtOH, a range of polyfused aryl-, indoyl-, and benzofuranyl-containing benzoisoindoles were isolated in moderate to good yields (39-74 %, Scheme 26). Mechanistically, after the initial oxidative addition of the Pd 0 species to the C-Br bond (80) and subsequent carbopalladiaton of the C-C triple bond (81), the authors suggested three possible pathways for the final cyclization, namely: i) electrophilic attack of the aromatic ring on the Pd center, ii) oxidative addition of the aromatic C-H bond to the Pd-C intermediate, and iii) carbometalation of the arene followed by β-hydride elimination.…”

Section: Use Of Organic Halides As Electrophile Precursorsmentioning

confidence: 99%

Innovative Catalytic Protocols for the Ring‐Closing Friedel–Crafts‐Type Alkylation and Alkenylation of Arenes

et al. 2006

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Over the past years an astonishing number of highly chemoand regioselective intramolecular Friedel-Crafts (IMFC)-type alkylations of aromatic compounds have been described in the literature that allow remarkable synthetic shortcuts for the preparation of challenging aromatic compounds. In particular, both transition metal and conventional and unusual Lewis acids (LAs) have been described to promote ring-clos- Index

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“…(40)) [468]. Palladium catalyzed an oxidative addition-alkyne insertion-bicyclopropylidene insertion to give cyclopropanated bi-, tri-, and tetracyclic frameworks [469].…”

Section: Carbon-carbon Bond Formation Via Insertion Of Alkynesmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Palladium‐Catalyzed Tandem Cyclization of Bromoenynes through Aromatic CH Bond Functionalization

Cited by 54 publications

References 57 publications

Dynamics of electrical double layer formation in room-temperature ionic liquids under constant-current charging conditions

Dynamics of electrical double layer formation in room-temperature ionic liquids under constant-current charging conditions

Innovative Catalytic Protocols for the Ring‐Closing Friedel–Crafts‐Type Alkylation and Alkenylation of Arenes

Transition metals in organic synthesis: Highlights for the year 2005

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