Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange

• Published in: Journal of organic chemistry Vol. 70; no. 7; pp. 2445 - 2454
• Main Authors: Sapountzis, Ioannis, Dube, Henry, Lewis, Robert, Gommermann, Nina, Knochel, Paul
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2005; Amer Chemical Soc
• Subjects: Alkali and alkaline-earth metals derivatives; Chemistry; Chemistry, Organic; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Science & Technology; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; ARYLMAGNESIUM; NITROARENES; CROSS-COUPLING REACTIONS; ORGANOMAGNESIUM REAGENTS; CHLORIDES; ARYL; GENERAL PREPARATION; GRIGNARD-REAGENTS; ZINC; Nitro compound; Organic iodine compounds; Grignard reagent; Stability; Organometallic compound; Aromatic compound; Magnesium Organic compounds; Exchange reaction; Chemical synthesis; Organic halogen compounds; Heterocyclic compound; Electrophile
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo048132o

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 °C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.