Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange

J Org Chem. 2005 Apr 1;70(7):2445-54. doi: 10.1021/jo048132o.

Abstract

[reaction: see text] Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40 degrees C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.