Palladium-catalyzed ring expansion reaction of 1-alkynylcyclobutanols with aryl iodides: an efficient route to 2-disubstituted methylenecyclopentanones |
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| Authors: | Li-Mei Wei Li-Lan Wei Wen-Bin Pan Ming-Jung Wu |
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| Affiliation: | a School of Chemistry, Kaohsiung Medicial University, Kaohsiung, Taiwan
b Fooyin University, Kaohsiung county, Taiwan |
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| Abstract: | The reaction of 1-alkynylcyclobutanols with aryl iodides in the presence of Pd(OAc)2 and Et3N in acetonitrile at 80°C for 24 h gives 2-disubstituted methylenecyclopentan-1-ones in modest to good yields. The tandem insertion-ring expansion process proceeds via the formation of an alkynyl π-complex, followed by migration of a carbon-carbon bond of the tert-alkanol to form the cyclopentanones stereoselectively. |
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| Keywords: | palladium and compounds ring expansion cyclopentanones |
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