Preparation of C 2-Symmetric Allenes by Palladium-Catalyzed Double-Nucleophilic Substitution on 3-Bromopenta-2,4-dienyl Acetate

Preparation of C 2-Symmetric Allenes by Palladium-Catalyzed Double-Nucleophilic Substitution on 3-Bromopenta-2,4-dienyl Acetate

Easily accessible 3-bromopenta-2,4-dienyl acetate was applied to the palladium-catalyzed reaction with soft nucleophiles. The reaction proceeded through the stepwise 2-fold nucleophilic substitution via formal SN2′ and SN2 processes giving the various doubly functionalized C 2-symmetric allenes in g...

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Veröffentlicht in:Journal of organic chemistry 2012-06, Vol.77 (12), p.5406-5410
Hauptverfasser: Ogasawara, Masamichi, Suzuki, Mayuka, Takahashi, Tamotsu
Format: Artikel
Sprache:eng
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Zusammenfassung:Easily accessible 3-bromopenta-2,4-dienyl acetate was applied to the palladium-catalyzed reaction with soft nucleophiles. The reaction proceeded through the stepwise 2-fold nucleophilic substitution via formal SN2′ and SN2 processes giving the various doubly functionalized C 2-symmetric allenes in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300511e