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Abstract
A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh3)3, and are highly dependent on the structure and reactivity of the starting ketenes.
Highlights
Ketenes are very important intermediates in the field of organic synthesis [1,2,3], and much attention has been focused on the ketene-metal complexes [4]
Treatment of alkyl phenyl ketenes 1a-c with internal alkynes 2 in the presence of 5 mol %
Treatment of diaryl ketenes 1d and e instead of alkyl phenyl ketenes 1a-c with internal alkynes 2 in the presence of the same RhCl(PPh3)3 catalyst (5 mol %) in mesitylene at 120 oC
Summary
Ketenes are very important intermediates in the field of organic synthesis [1,2,3], and much attention has been focused on the ketene-metal complexes [4]. We developed the novel RhCl(PPh3)3-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes and a novel synthesis of furans by the unusual RhCl(PPh3)3-catalyzed cycloaddition of diaryl ketenes with internal alkynes. In these reactions, the catalyst is the same but the products are completely different, depending on the structure and reactivity of the starting ketenes
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