Ir-Catalyzed Intermolecular Branch-Selective Allylic C–H Amidation of Unactivated Terminal Olefins
2019; American Chemical Society; Volume: 141; Issue: 6 Linguagem: Inglês
10.1021/jacs.9b00237
ISSN1943-2984
Autores Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoAn efficient method for intermolecular branch-selective allylic C–H amidation has been accomplished via Ir(III) catalysis. The reaction proceeds through initial allylic C–H activation, supported by the isolation and crystallographic characterization of an allyl-Ir(III) intermediate, followed by a subsequent oxidative amidation with readily available dioxazolones as nitrenoid precursors. A diverse range of amides are successfully installed at the branched position of terminal alkenes in good yields and regioselectivities. Importantly, the reaction allows the use of amide-derived nitrenoid precursors avoiding problematic Curtius-type rearrangements.
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