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Synlett 1990; 1990(12): 773-774
DOI: 10.1055/s-1990-21248
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Sequential Radical Cyclization/Organometallic Addition. On the Mechanism of the Samarium(II) Mediated Barbier Reaction in the Presence of Hexamethylphosphoric Triamide

Dennis P. Curran* , Thomas L. Fevig, Michael J. Totleben
  • *Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
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Publication Date:
08 March 2002 (online)

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Samarium(II) iodide mediated aryl radical cyclization of 1-allyloxy-2-iodobenzene in the presence of hexamethyl-phosphoric triamide (HMPA) produces a solution-stable organo-samarium intermediate that can be trapped with electrophiles (6 examples) or with aldehydes and ketones (Barbier-type coupling, 8 examples). These results suggest that traditional samarium(II) mediated Barbier reactions often proceed by an organometallic addition mechanism.

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