Pd0‐Catalyzed Coupling Cyclization Reaction of Aryl or 1Alkenyl Halides with 1,2‐Allenyl Ketones: Scope and Mechanism. An Efficient Assembly of 2,3,4‐, 2,3,5‐Tri‐ and 2,3,4,5‐Tetrasubstituted Furans
- 28 May 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (11) , 2447-2456
- https://doi.org/10.1002/chem.200204664
Abstract
Described herein is the Pd0-catalyzed coupling cyclization reaction of 1,2-allenyl ketones with organic halides leading efficiently and conveniently to not only 2,3,4- and 2,3,5-trisubstituted furans but also 2,3,4,5-tetrasubstituted furans. Furthermore, this method showed high substituent-loading capability and tolerance of various substituents. The reactions of 1,2-allenyl ketones 1 e, 1 p, 1 q, and deuterated [D]1 c were performed for a mechanistic study, which demonstrated that instead of an enolization pathway, the reaction may proceed via the intermediacy of dienolate palladium and intramolecular nucleophilic attack on the π-allyl palladium intermediate by the carbonyl oxygen.Keywords
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