The Grubbs reaction is a method for achieving olefin metathesis using ruthenium (Ru) carbene catalysts (the Grubbs catalyst series), developed by Professor Robert H. Grubbs.
Olefin metathesis was first discovered by accident in the 1950s. It refers to the process in which olefins, in the presence of metal carbene catalysts, undergo cleavage of carbon-carbon double bonds and recombine to form new olefin molecules. This reaction can efficiently construct various new olefin structures, allowing for the design of complex molecular frameworks, especially in the synthesis of macrocyclic compounds, polycyclic structures, and complex natural products.
Reagents: Grubbs catalyst, Solvent
Reactants: Olefin
Products: Olefin
Reaction Type: Metathesis Reaction
Experimental Tips:
Grubbs catalysts are the most widely used of catalysts for olefin metathesis：
The first-generation Grubbs catalyst, with the chemical formula RuCl₂(=CHPh)(PCy₃)₂, is relatively stable to air and moisture but exhibits limited tolerance toward certain functional groups, such as polar moieties.
The second-generation Grubbs catalyst replaces one phosphine ligand of the first-generation catalyst with an N‑heterocyclic carbene ligand. Compared to the first-generation catalyst, it exhibits faster reaction rates, higher selectivity, and broader functional group compatibility (e.g., tolerance toward ester, amino, and other polar groups).
The third-generation Grubbs catalyst is developed by replacing the phosphine ligand in the second-generation catalyst with a pyridine ligand. This modification significantly enhances the catalytic activity (reaction rate) of the Grubbs catalyst system.
Reaction Mechanism:
Original Literature:
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Related Reactions
Related Compounds
- Olefin
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