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
Hauptverfasser: Taylor, Richard E, Ciavarri, Jeffrey P
Format: Artikel
Sprache:eng
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9900865