Abstract
The great impact of the nanoscale organization of reactive species on their performance in chemical transformations creates the possibility of fine-tuning of reaction parameters by modulating the nano-level properties. This methodology is extensively applied for the catalysts development whereas nanostructured reactants represent the practically unexplored area. Here we report the palladium- and copper-catalyzed cross-coupling reaction involving nano-structured nickel thiolate particles as reagents. On the basis of experimental findings we propose the cooperative effect of nano-level and molecular-level properties on their reactivity. The high degree of ordering, small particles size, and electron donating properties of the substituents favor the product formation. Reactant particles evolution in the reaction is visualized directly by dynamic liquid-phase electron microscopy including recording of video movies. Mechanism of the reaction in liquid phase is established using on-line mass spectrometry measurements. Together the findings provide new opportunities for organic chemical transformations design and for mechanistic studies.
Highlights
The great impact of the nanoscale organization of reactive species on their performance in chemical transformations creates the possibility of fine-tuning of reaction parameters by modulating the nano-level properties
We have recently shown that 1Dnanostrucutured metal thiolates and their functional derivatives provide an efficient opportunity for selective catalytic carbonheteroatom bond formation[49,50]
We report the real-time observation of the involvement of a nanostructured reagent in a cross-coupling reaction (Fig. 1c) performed by advanced liquid-phase electron microscopy (Fig. 1b)
Summary
The great impact of the nanoscale organization of reactive species on their performance in chemical transformations creates the possibility of fine-tuning of reaction parameters by modulating the nano-level properties. We report the real-time observation of the involvement of a nanostructured reagent in a cross-coupling reaction (Fig. 1c) performed by advanced liquid-phase electron microscopy (Fig. 1b). Direct liquid-phase microscopic monitoring of the C–S cross-coupling reaction, as well as Electrospray Ionization Mass Spectrometry (ESI-MS) and kinetic measurements in solution reveal the key features of the nanostructured reagents a Standard electron microscopy
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