Sequential Radical Cyclization/Organometallic Addition. On the Mechanism of the Samarium(II) Mediated Barbier Reaction in the Presence of Hexamethylphosphoric Triamide
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (12) , 773-774
- https://doi.org/10.1055/s-1990-21248
Abstract
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.Keywords
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