Iron (II) Ion Catalysed Synthesis of a-Aryl and a-Alkylthioacetylamides

MURGUÍA, M.C.; RICCI, C.G.; CABRERA, M.I.; LUNA, J.A.; GRAU, R.J.A.

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2001 p. 113 - 120

1381-1169

The potential of iron(II)-catalysed reactions the synthesis of a-aryl and a-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?1.6 mol% range are large enough to reach yields of 86% of a-phenil-N-thioacetylmorpholine 3a and 65% of a-(1-adamanthyl)-N-thioacetyl-morpholine 3b. These catalytic reactions are more easily handled than photoinduced reactions, and provide a useful route to the synthesis of a-aryl and a-alkyl thioacetylamides from acetylthiomides without the need for special photochemical devices. A possible reaction pathway is suggested for the iron(II)-catalysed process involving iron-thioamide enolate complexes.