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

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posted on 2004-07-28, 00:00 authored by Douglas B. Grotjahn, Justin M. Hoerter, John L. Hubbard
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.