Palladium(0)-Catalyzed Allylation of Highly Acidic and Nonnucleophilic Anilines. the Origin of Stereochemical Scrambling When Using Allylic Carbonates

Marcial Moreno-Mañas, Lurdes Morral, Roser Pleixats

Research output: Contribution to journalArticleResearchpeer-review

55 Citations (Scopus)

Abstract

Acidic anilines such as diphenylamine, phenothiazine, and nitroanilines are efficiently allylated under palladium catalysis using allyl carbonates as allylating reagents. A stereochemical study of the reactions of ethyl cis-5-methyl-2-cyclohexenylcarbonate with 4-nitro- and 2,4-dinitroaniline was performed. Bidentate phosphines as stabilizing ligands gave clean retention of configuration whereas triphenylphosphine permitted cis-trans isomerization of the allylic carbonate, the allylation reactions occurring under Curtin-Hammet preequilibrium conditions.
Original languageEnglish
Pages (from-to)6160-6166
JournalJournal of Organic Chemistry
Volume63
Issue number18
DOIs
Publication statusPublished - 4 Sep 1998

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