A reaction of imidazo[1,2-α]pyridine and Zhdankin reagent (IBA-N3) is described for the synthesis of α-iminonitriles via visible light photoredox catalysis. A series of substituted α-iminonitriles were efficiently prepared in moderate to good yiel...
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UVA LED Light Promoted Cross‐Coupling of Tertiary α‐Silylamines with 1‐Iodoalkynes
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A synthetic method to prepare propargyl amines efficiently from tertiary α-silylamines and 1-iodoalkynes under UVA LED light is described. Achieved under mild reaction conditions at room temperature, the site- and chemoselective approach was shown to tolerate a wide variety of substrates and be applicable to the late-stage functionalisation of a variety of bioactive compounds.
Abstract
A synthetic strategy that exploits the formation of an electron donor-acceptor (EDA) complex between a tertiary α-silylamine and 1-iodoalkyne under UVA LED (light emitting diode) light (λ max=365 nm) to prepare propargyl amines is described. The site- and chemoselective synthetic method was shown to tolerate a wide range of functional groups to give the α-alkynylation product in good to excellent yields. The usefulness of the C(sp)–C(sp3) bond formation protocol was also exemplified by the late-stage functionalisation of a variety of natural products and bioactive compounds.
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