49742-56-5Relevant articles and documents
Miniaturized catalysis: monolithic, highly porous, large surface area capillary flow reactors constructed in situ from polyhedral oligomeric silsesquioxanes (POSS)
Scholder,Nischang
, p. 3917 - 3921 (2015)
A single-step molding process utilizing free-radical cross-linking reaction of vinyl POSS in microliter-sized dimensions leads to hierarchically-structured, mechanically robust, porous hybrid structures. Functional variants show excellent performance in Suzuki-type coupling reactions. Due to their small volume, long-term operational robustness, and potential chemical diversity, these materials are promising candidates for catalyst screening applications.
Micellar catalysis of the Suzuki Miyaura reaction using biogenic Pd nanoparticles fromDesulfovibrio alaskensis
Dennis, Jonathan A.,Era, Yuta,Horsfall, Louise E.,Wallace, Stephen
supporting information, p. 8886 - 8890 (2021/11/23)
Microorganisms produce metal nanoparticles (MNPs) upon exposure to toxic metal ions. However, the catalytic activity of biosynthesised MNPs remains underexplored, despite the potential of these biological processes to be used for the sustainable recovery of critical metals, including palladium. Herein we report that biogenic palladium nanoparticles generated by the sulfate-reducing bacteriumDesulfovibrio alaskensisG20 catalyse the ligand-free Suzuki Miyaura reaction of abiotic substrates. The reaction is highly efficient (>99% yield, 0.5 mol% Pd), occurs under mild conditions (37 °C, aqueous media) and can be accelerated within biocompatible micelles at the cell membrane to yield products containing challenging biaryl bonds. This work highlights how native metabolic processes in anaerobic bacteria can be combined with green chemical technologies to produce highly efficient catalytic reactions for use in sustainable organic synthesis.
Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight
Dorval, Céline,Tricoire, Maxime,Begouin, Jeanne-Marie,Gandon, Vincent,Gosmini, Corinne
, p. 12819 - 12827 (2020/11/18)
Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.
