Carbonyl allylation in the absence of preformed allyl metal reagents: Reverse Prenylation via iridium-catalyzed hydrogenative coupling of dimethylallene

Eduardas Skucas, John F. Bower, Michael J. Krische

Research output: Contribution to journalArticle (Academic Journal)peer-review

62 Citations (Scopus)

Abstract

Iridium-catalyzed hydrogenation of dimethylallene in the presence of aromatic, heteroaromatic, and aliphatic carbonyl electrophiles 1a-12a delivers products of reverse prenylation 1b-12b. Reductive coupling of dimethyl allene to aldehyde 8a under an atmosphere of deuterium provides deuterio -8b. As revealed by H-2 NMR analysis, deuterium incorporation is observed at the vinylic position (80% H-2). Unlike established methods for carbonyl allylation, the present protocol circumvents the use of stoichiometrically preformed organometallic reagents.

Original languageEnglish
Pages (from-to)12678-+
Number of pages3
JournalJournal of the American Chemical Society
Volume129
Issue number42
DOIs
Publication statusPublished - 24 Oct 2007

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