Abstract
Olefin metathesis has emerged as one of the most widely used transformations in organic synthesis for the formation of carbon-carbon double bonds. Grela and coworkers described the performance of unmodified, commercially available olefin metathesis catalysts in water in the absence of surfactants. The ultrasonication of water-insoluble substrates and catalysts in water allowed the formation of emulsions in which smooth catalytic ring-closing metathesis (RCM), cross-metathesis (CM), and enyne metathesis took place in excellent yields. Grubbs and coworkers explored a number of modified catalysts that impart water solubility, allowing reactions using water as the reaction medium. The poly(ethylene glycol) (PEG)-tagged Hoveyda-type catalyst, that is active and stable in water, and showed good activity in ring opening metathesis polymerization (ROMP) and RCM reactions of water-soluble dienes in an aqueous medium. Other water-soluble catalysts containing polar quaternary ammonium groups in the benzylidene fragment were later reported by Grubbs and Grela.
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