2-Bromoallyl Acetate: A Useful Structural Unit for Sequential Carbon−Carbon Bond Formation
2-Bromoallyl acetate has been shown to be an efficient substrate for Ni(II)/Cr(II)-mediated coupling reactions with a variety of aliphatic and aryl aldehydes. Surprisingly, elimination of acetate from the intermediate vinylchromium species does not appear to compete with carbon−carbon bond formation...
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Veröffentlicht in: | Organic letters 1999-08, Vol.1 (3), p.467-470 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 2-Bromoallyl acetate has been shown to be an efficient substrate for Ni(II)/Cr(II)-mediated coupling reactions with a variety of aliphatic and aryl aldehydes. Surprisingly, elimination of acetate from the intermediate vinylchromium species does not appear to compete with carbon−carbon bond formation. In addition, the allylic acetate products have been shown to be useful allyl nucleophile precursors through palladium-mediated reactions. These results suggest that acyloxyalkenyl bromides are efficient linchpins for multiple carbon−carbon bond formation. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol9900865 |