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Diazovinylation.pdf (16.93 MB)
Copper-Catalyzed Insertion of Diazo Compounds into Vinyl Hypervalent Iodine Reagents to Generate Allylic Esters
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submitted on 26.03.2019 and posted on 27.03.2019by Guillaume Pisella, Alec Gagnebin, Jerome Waser
unprecedented copper(I)-catalyzed vinylation of (donor)-acceptor
with VinylBenziodoXolone reagents (VBX) as partners is reported. The
transformation tolerates variation of both donor- and acceptor substituents on
the diazo compounds, delivering the corresponding benzoylated allylic alcohol
products in good to excellent yields. Through the development of a protocol for
the synthesis of functionalized alkanes-, dienes- and enynes-substituted VBX
reagents, a broad scope of substituents on the alkene could be accessed. The
obtained products contain synthetically versatile functional groups, such as an
aryl iodide, an ester and an allylic leaving group, enabling selective further