Nucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents.
Angew Chem Int Ed Engl
; 60(42): 22915-22924, 2021 Oct 11.
Article
em En
| MEDLINE
| ID: mdl-34414643
ABSTRACT
The heptafluoroisopropyl group (CF(CF3 )2 ) is prevalent in pharmaceuticals and agrichemicals. However, heptafluoroisopropoxylated (OCF(CF3 )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(CF3 )2 reagents. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines with AgCF(CF3 )2 . The substitutions on the nitrogen atom significantly affected the properties and reactivities of N-OCF(CF3 )2 reagents. Accordingly, two types of N-OCF(CF3 )2 reagents including N-OCF(CF3 )2 phthalimide A and N-OCF(CF3 )2 benzotriazolium salt O' were used as OCF(CF3 )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.
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MEDLINE
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En
Ano de publicação:
2021
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Article