Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates

Porzelle, Achim and Woodrow, Michael D. and Tomkinson, Nicholas C. O. (2009) Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates. Synlett (5). pp. 798-802. ISSN 0936-5214

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Abstract

An efficient 1-pot procedure for the Zn-mediated redn. of nitro arenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixts. in good to excellent yield (34-81%). Solvolysis of the bisprotected hydroxylamines with NaOMe at room temp. provides access to synthetically versatile N-aryl-N-hydroxy carbamates in excellent yields (89-97%).