Oxidative nucleophilic substitution of hydrogen in nitro(pentafluorosulfanyl)benzenes with alkyl Grignard and lithium reagents

Alkyl Grignard and lithium reagents underwent nucleophilic addition to para- and meta-nitro(pentafluorosulfanyl)benzenes in ether solvents to form σH adducts, which were oxidized with potassium permanganate in liquid ammonia to yield products of oxidative nucleophilic substitution of hydrogen in moderate to good yields.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Oxidative nucleophilic substitution of hydrogen in nitro(pentafluorosulfanyl)benzenes with Grignard and lithium reagents was investigated. ► Addition of potassium permanganate in liquid ammonia significantly increases the yield of ONSH products. ► ONSH reaction take place in ortho- and para-positions relative to the nitro group.