期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 25, 页码 9198-9203出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501106
关键词
allenes; annulation; carboxylic acids; CH activation; reaction mechanisms; rhodium
资金
- Ministry of Science and Technology of the Republic of China [MOST-103-2633M-007-001]
A highly regio- and stereoselective synthesis of 3,3-disubstituted phthalides from aryl carboxylic acids and allenes using a rhodium(III) catalyst has been demonstrated. The reaction features broad functional group tolerance and provides a simple and straightforward route to the synthesis of various 3-vinyl-substituted phthalides. Furthermore, the catalytic reaction can also be applied to the synthesis of biologically active 5-vinyl-substituted 2-furanones from ,-unsaturated carboxylic acids and allenes. The reactions proceed through a carboxylate-assisted ortho-CH activation and [4+1] annulation. The preliminary mechanistic studies suggest that a CH cleavage is the rate-determining step.
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