Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched beta-arylethylamines

Jeremy Robertson, Matthew J. Palframan, Stephen A. Shea, Kirill Tchabanenko, William R. Unsworth, Chase Winters

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

5-exo Cyclisation of vinyl-, aryl- and alkyl-radicals onto the aryl group of arylcarboxamides is followed by beta-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or beta-arylethylamines.
Original languageEnglish
Pages (from-to)11896-11907
Number of pages12
JournalTetrahedron
Volume64
Issue number52
DOIs
Publication statusPublished - 22 Dec 2008

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