Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group

The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the ol...

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Veröffentlicht in:Journal of organic chemistry 2011-05, Vol.76 (9), p.3024-3033
Hauptverfasser: Mochida, Satoshi, Hirano, Koji, Satoh, Tetsuya, Miura, Masahiro
Format: Artikel
Sprache:eng
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Zusammenfassung:The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo200509m