Premium
One‐Pot Transformation of Methylarenes into Aromatic Aldehydes under Metal‐Free Conditions
Author(s) -
Tabata Masayuki,
Moriyama Katsuhiko,
Togo Hideo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402015
Subject(s) - chemistry , reagent , acetonitrile , transformation (genetics) , transition metal , oxide , organic chemistry , tungsten , aromaticity , catalysis , molecule , biochemistry , gene
On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N ‐methylmorpholine N ‐oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A ) or with NBS in CCl 4 under irradiation with a tungsten lamp at 30 °C (Method B ), followed by treatment with N ‐methylmorpholine N ‐oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one‐pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals.