γ,δ,ε-C(sp3)–H Functionalization through Directed Radical H-Abstraction
Journal of the American Chemical Society2015Vol. 137(18), pp. 5871–5874
Citations Over TimeTop 10% of 2015 papers
Abstract
Aliphatic amides are selectively functionalized at the γ- and δ-positions through directed radical 1,5 and 1,6 H-abstractions, respectively. The initially formed γ- or δ-lactams are intercepted by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the γ-, δ-, and ε-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.
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