Double C−H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(I) Using Alkynes. Synthesis of 1,4-Dien-3-ones

Double C−H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(I) Using Alkynes. Synthesis of 1,4-Dien-3-ones

Under the influence of an Ir(I) metal fragment, the methyl group of phenyl(methyl)ketene undergoes two C−H activations in reacting with internal alkynes, giving metallacycles 3 in 86−94% yield. Treatment of 3 with CO liberates 1,4-dien-3-ones 5 in 81−93% yield, along with CO complex 4. A possible me...

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Veröffentlicht in:Journal of the American Chemical Society 2004-07, Vol.126 (29), p.8866-8867
Hauptverfasser: Grotjahn, Douglas B, Hoerter, Justin M, Hubbard, John L
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung:Under the influence of an Ir(I) metal fragment, the methyl group of phenyl(methyl)ketene undergoes two C−H activations in reacting with internal alkynes, giving metallacycles 3 in 86−94% yield. Treatment of 3 with CO liberates 1,4-dien-3-ones 5 in 81−93% yield, along with CO complex 4. A possible mechanism for the very selective double C−H activation−alkyne coupling is discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja048489+