Nucleophilic and Radical Heptafluoroisopropoxylation with Redox‐Active Reagents
Chao‐Lai Tong, Xiu‐Hua Xu, Feng‐Ling Qing
Abstract
Abstract The heptafluoroisopropyl group (CF(CF 3 ) 2 ) is prevalent in pharmaceuticals and agrichemicals. However, heptafluoroisopropoxylated (OCF(CF 3 ) 2 ) compounds remain largely underexplored, presumably due to the lack of efficient access to these compounds. Herein, we disclose the practical and efficient heptafluoroisopropoxylation reactions through the invention of a series of redox‐active N ‐OCF(CF 3 ) 2 reagents. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines with AgCF(CF 3 ) 2 . The substitutions on the nitrogen atom significantly affected the properties and reactivities of N ‐OCF(CF 3 ) 2 reagents. Accordingly, two types of N ‐OCF(CF 3 ) 2 reagents including N ‐OCF(CF 3 ) 2 phthalimide A and N ‐OCF(CF 3 ) 2 benzotriazolium salt O′ were used as OCF(CF 3 ) 2 anion and radical precursors, respectively. This protocol enables the direct heptafluoroisopropoxylation of a range of substrates, delivering the corresponding products in moderate to excellent yields.