Preparation of benzo[b]thiophenes by Pd(0)-catalyzed intramolecular cyclization of allyl (and propargyl) o-iodophenyl sulfides.

Narcís Arnau, Marcial Moreno-Mañas, Roser Pleixats

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Abstract

Benzo[b]thiophenes are prepared by intramolecular Pd(0)-catalyzed Heck reaction of allyl o-iodophenyl sulfides. Pd(0)-Catalyzed intramolecular cyclization of o-iodophenyl propargyl sulfide in the presence of a hydride donor gives 3-methylene-2,3-dihydrobenzo[b]thiophene, which reacts with several enophiles in ene type reactions. However, allyl (and propargyl) aryl sulfides react with palladium(II) chloride to afford polymeric [PdCl(SAr)]2. © 1993.
Original languageEnglish
Pages (from-to)11019-11028
JournalTetrahedron
Volume49
Issue number47
DOIs
Publication statusPublished - 1 Jan 1993

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