Double C-H activation during functionalization of phenyl(methyl)ketene on iridium(I) using alkynes. synthesis of 1,4-dien-3-ones

Douglas B Grotjahn; Justin M Hoerter; John L Hubbard

doi:10.1021/ja048489+

Double C-H activation during functionalization of phenyl(methyl)ketene on iridium(I) using alkynes. synthesis of 1,4-dien-3-ones

J Am Chem Soc. 2004 Jul 28;126(29):8866-7. doi: 10.1021/ja048489+.

Authors

Douglas B Grotjahn¹, Justin M Hoerter, John L Hubbard

Affiliation

¹ Department of Chemistry, San Diego State University, 5500 Campanile Drive, San Diego, California 92182-1030, USA. [email protected]

PMID: 15264796
DOI: 10.1021/ja048489+

Abstract

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.