General Preparation of Functionalized<i>o</i>-Nitroarylmagnesium Halides through an Iodine-Magnesium Exchange

Abstract

Highly functionalized aryl Grignard reagents with an ortho-nitro substituent have been synthesized from 2-iodonitroaryl compounds through an I–Mg exchange reaction with PhMgCl or mesityl magnesium bromide (see scheme). These reagents are stable (T<−20°C for several hours) and undergo various cross-coupling reactions in the presence of Cu or Pd catalysts (dba = trans,trans-dibenzylideneacetone; tfp = tri-o-furylphosphane).