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Synthesis of Fluoranthene Derivatives via Tandem Suzuki-Miyaura and Intramolecular C-H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions.

ABSTRACT: A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki-Miyaura and intramolecular C-H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl₂ as well as heterogeneous catalysis using reduced graphene oxide (rGO)-CuPd nanocatalysts with low catalyst loadings. High functional group tolerance is observed under both catalytic conditions where arylboronic acids and esters having electron-withdrawing and electron-donating substituents afforded fluoranthene products in good yields (up to 78%). Moreover, the rGO-CuPd nanocatalysts are demonstrated to be reusable by preserving almost 90% of their initial activity after the third cycle.

SUBMITTER: Pal S

PROVIDER: S-EPMC6645568 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Synthesis of Fluoranthene Derivatives via Tandem Suzuki-Miyaura and Intramolecular C-H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions.

Pal Sujit S Metin Önder Ö Türkmen Yunus E YE

ACS omega 20171207 12

A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki-Miyaura and intramolecular C-H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl<sub>2</sub> as well as heterogeneous catalysis using reduced graphene oxide (rGO)-CuPd nanocatalysts with low catalyst loadings. High functional group tolerance is observed under both catalytic conditions where arylboronic acids and esters having ...[more]

PMID: 31457400

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Supramolecular Linear-Dendritic Nanoreactors: Synthesis and Catalytic Activity in "Green" Suzuki-Miyaura Reactions.

Project description:This study describes the synthesis of novel amphiphilic linear-dendritic block copolymers and their self-assembly in water to form supramolecular nanoreactors capable of catalyzing Suzuki-Miyaura coupling reactions under "green" conditions. The block copolymers were formed through copper(I)-catalyzed alkyne-azide cycloaddition between azide functionalized poly(benzyl ether) dendrons as the perfectly branched blocks, as well as bis-alkyne modified poly(ethylene glycol), PEG, as the linear block. A first-generation poly(benzyl ether) dendron (G1) was coupled to a bis-alkyne modified PEG with molecular mass of 5 kDa, forming an ABA copolymer (G1)2-PEG5k-(G1)2 (yield 62%), while a second-generation dendron (G2) was coupled to a 11 kDa bis-alkyne modified PEG to produce (G2)2-PEG11k-(G2)2 (yield 49%). The structural purity and low dispersity of the linear-dendritic copolymers were verified by size-exclusion chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Their self-assembly was studied by dynamic light scattering, showing that (G1)2-PEG5k-(G1)2 and (G2)2-PEG11k-(G2)2 formed single populations of micelles (17 nm and 37 nm in diameter, respectively). The triazole rings located at the boundaries between the core and the corona are efficient chelating groups for transition metals. The ability of the micelles to complex Pd was confirmed by 1H NMR, transmission electron microscopy, and inductively coupled plasma. The catalytic activity of the supramolecular linear-dendritic/Pd complexes was tested in water by model Suzuki-Miyaura reactions in which quantitative yields were achieved within 3 h at 40 °C, while, at 17 °C, a yield of more than 70% was attained after 17 h.

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Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki-Miyaura Coupling Reactions.

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Project description: Not available

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