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General Preparation of Functionalized o ‐Nitroarylmagnesium Halides through an Iodine–Magnesium Exchange
Author(s) -
Sapountzis Ioannis,
Knochel Paul
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020503)41:9<1610::aid-anie1610>3.0.co;2-t
Subject(s) - reagent , chemistry , aryl , bromide , iodine , magnesium , substituent , halide , magnesium bromide , catalysis , medicinal chemistry , coupling reaction , inorganic chemistry , polymer chemistry , organic chemistry , alkyl
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).