Salt Metathesis Mechanism

Salt Metathesis Mechanism-90
These results suggest how important the role of the hydrophobic effect is on the catalytic activity of the reaction.

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Although challenging, the possibility to perform aqueous metatheses has become an attractive alternative, not only because water is a more sustainable medium, but also to exploit biocompatible conditions.

This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology.

Keywords: Olefin metathesis represents a versatile synthetic tool for the construction of carbon–carbon bonds [1-9].

Since its first report in 1956, a Ti(II)-catalyzed polymerization of norbornene [10], metathesis rapidly attracted interest among organic chemists and has been used in different research fields spanning polymer chemistry [11,12] to drug discovery [13-15].

In this specific case, the formation of the metal hydride complex is believed to occur during the work-up with methanol.

Dinger and Mol also carried out studies supporting this theory [30]. Wiley Online Library requires cookies for authentication and use of other site features; therefore, cookies must be enabled to browse the site.Detailed information on how Wiley uses cookies can be found in our Privacy Policy.There is a growing interest in performing metathesis reactions in water as a greener alternative to chlorinated or aromatic solvents [23,24].Water is inexpensive, non-flammable, non-toxic and environmentally friendly, all characteristics that make it an ideal solvent.This visionary mechanistic proposal was later confirmed by experimental studies [17-20].Ruthenium-based catalysts are among the most tolerant and stable metathesis catalysts and are widely employed for metatheses in aqueous media [21,22].In their report, they elucidated the degradation pathway of the first generation Grubbs catalyst (G-I) in the presence of primary alcohols and water (Scheme 4).The detrimental effect of water is more likely to occur at high temperatures and in the presence of a base.The catalytic cycle involves an initial [2 2] cycloaddition between a metal carbene I and an olefin, followed by a retro [2 2] cycloaddition, leading to the release of a “scrambled” olefin (e.g., ethylene in Scheme 2) and the metal carbene species III as key intermediate.A [2 2] cycloaddition with a second olefin leads to the formation of intermediate IV, followed by a retro [2 2] cycloaddition that regenerates catalyst I and releases the metathesis product.


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