Iron(II) ion-catalysed synthesis of alpha-aryl and alpha-alkylthioacetylamides

The potential of iron(II)-catalysed reactions the synthesis of alpha -aryl and alpha -alkyl thioacetylamides from acetylthiomides is reported. Iron(II ) ion efficiently catalyses reactions of iodobenzene 1a or 1-iodoadamantane 1b with N-thioacetylmorpholine anion 2 in DMSO. Ferrous bromide amounts in the 0.6-1.6mol% range are large enough to reach yields of 86% of alpha -ph enil-N-thioacetylmorpholine 3a and 65% of alpha-(1-adamanthyl)-N-thioacetyl -morpholine 3b. These catalytic reactions are more easily handled than phot oinduced reactions, and provide a useful route to the synthesis of or-aryl and ol-alkyl thioacetylamides from acetylthiomides without the need for spe cial photochemical devices. A possible reaction pathway is suggested for th e iron(II)-catalysed process involving iron-thioamide enolate complexes. (C ) 2001 Elsevier Science B.V. All rights reserved.