2020
DOI: 10.1021/acs.organomet.0c00113
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Synthesis of the Cationic Gallium Phthalocyanines and Their Catalytic Application in Gallium(III)-Activated Processes for Donor–Acceptor Substrates

Abstract: The novel class of gallium catalysts based on cationic gallium phthalocyanines (RPcGa+) with SbF6 – and Sb2F11 – weakly coordinating anions was developed in order to using in the catalytic version for gallium-specific chemistry. Two cycloaddition/annulation processes of styrylmalonates with aromatic aldehydes and styrene were implemented in the catalytic version using this approach. The synthetic strategy to gallium phthalocyanines and their structural features were studied in details, including the use of spe… Show more

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Cited by 22 publications
(5 citation statements)
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“…Such distances are typical for molecules arranged by π−π stacking in Pc crystallography. 34,36 The ligands do not form a perfect vertical cofacial stack in gallium dimers but are displaced, and such a shifted overlap stabilizes the dimerization by the offset π-stacked interaction 37 of two phthalocyaninate ligands. Thus, in the case of obtained supramolecular dimers, there are two different forces that bring Pc ligands close to each other: coordination of the alkali cations by the crown-ether substituents and π−π interaction.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Such distances are typical for molecules arranged by π−π stacking in Pc crystallography. 34,36 The ligands do not form a perfect vertical cofacial stack in gallium dimers but are displaced, and such a shifted overlap stabilizes the dimerization by the offset π-stacked interaction 37 of two phthalocyaninate ligands. Thus, in the case of obtained supramolecular dimers, there are two different forces that bring Pc ligands close to each other: coordination of the alkali cations by the crown-ether substituents and π−π interaction.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Over the years and continuing into the present, a substantial amount of research has been conducted on the experimental preparation and characterization of this series of post-transition metals combined with phthalocyanine (PM–Pc), with relevant studies confirming their specific applications within these synthesized nanosheets. For instance, the successfully synthesized Al–Pc retains its paramagnetic properties and has been effectively used in spin switching devices; the experimentally produced Ga–Pc serves as a catalyst for cycloaddition/annulation processes in organic synthesis; the In–Pc synthesized in the laboratory has applications in medicine against Staphylococcus aureus and Escherichia coli , as well as in humidity sensors; , the Tl–Pc, experimentally synthesized, has been confirmed to possess nonlinear optical properties; the Ge–Pc, synthesized in laboratory studies, features unique antiaromatic π-electron circuits; the Sn–Pc, also experimentally synthesized, is a promising candidate for low-cost organic electronic devices, which can be utilized in organic thin-film transistors (OTFTs) and organic photovoltaics (OPVs); The Pb–Pc, also prepared in the laboratory, can effectively influence nanoscale charge transport through humidity control to enhance conductance and can be regarded as a prototypical material suitable for application in molecular materials. , Lastly, experiments on synthesizing Bi–Pc are relatively scarce, with only two similar structural syntheses published to date. , …”
Section: Introductionmentioning
confidence: 99%
“…A likely mechanism of the process can be presented as follows (Scheme ). In the first stage, β-styrylmalonate 1 is activated by gallium trichloride and aldehyde 2 is protonated to generate an ion pair ( I + II ), as discussed previously , in the reaction of styrylmalonates with aromatic aldehydes . This process activates the formation of a C–C bond to give intermediate III that undergoes cyclization into intermediate V with high trans diastereoselectivity (Scheme ), directly or after elimination of a water molecule.…”
mentioning
confidence: 98%
“…The data about the synthesis and chemical properties of β-styrylmalonates available in the literature are rather fragmentary. , These data were expanded by our team. A series of works devoted to the reactions of aromatic aldehydes with β-styrylmalonates 1 in the presence of various Lewis acids and under various reaction conditions were published. , Moreover, new ways to synthesize indene , and dihydropyranone structures, polycyclic lactones, and asymmetrically substituted 1,4-(cyclopentathienyl)­benzenes were suggested (Scheme A).…”
mentioning
confidence: 99%