PREPARATION OF BENZO[B]THIOPHENES BY PD(0)-CATALYZED INTRAMOLECULAR CYCLIZATION OF ALLYL (AND PROPARGYL) O-IODOPHENYL SULFIDES

Authors
ARNAU N MORENOMANAS M PLEIXATS R
Citation
N. Arnau et al., PREPARATION OF BENZO[B]THIOPHENES BY PD(0)-CATALYZED INTRAMOLECULAR CYCLIZATION OF ALLYL (AND PROPARGYL) O-IODOPHENYL SULFIDES, Tetrahedron, 49(47), 1993, pp. 11019-11028
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
47
Year of publication
1993
Pages
11019 - 11028
Database
ISI
SICI code
0040-4020(1993)49:47<11019:POBBPI>2.0.ZU;2-F
Abstract
Benzo[b]thiophenes are prepared by in intramolecular Pd(O)-catalyzed H eck reaction of allyl o-iodophenyl sulfides. Pd(O)-Catalyzed intramole cular 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 affo rd polymeric [PdCl(SAr)]2.