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?,?,?-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

ABSTRACT: Aliphatic amides are selectively functionalized at the ?- and ?-positions through directed radical 1,5 and 1,6 H-abstractions, respectively. The initially formed ?- or ?-lactams are intercepted by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the ?-, ?-, and ?-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.

SUBMITTER: Liu T

PROVIDER: S-EPMC4431913 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

Liu Tao T Mei Tian-Sheng TS Yu Jin-Quan JQ

Journal of the American Chemical Society 20150430 18

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. ...[more]

PMID: 25915558

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