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Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes

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journal contribution
posted on 28.09.2011, 00:00 by Masato Ohashi, Tomoaki Taniguchi, Sensuke Ogoshi
Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C–O bond activation. However, no cycloaddition reaction involving their C–O bond activation has been demonstrated thus far. The present study developed a Ni(0)-catalyzed unique [3+2] cycloaddition reaction of α,β-unsaturated phenyl esters with alkynes in iPrOH to yield cyclopentenone derivatives.