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Copper-Catalyzed Insertion of Diazo Compounds into Vinyl Hypervalent Iodine Reagents to Generate Allylic Esters

preprint
submitted on 26.03.2019 and posted on 27.03.2019 by Guillaume Pisella, Alec Gagnebin, Jerome Waser
An unprecedented copper(I)-catalyzed vinylation of (donor)-acceptor diazo compounds 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 modification.

Funding

European Research Council Starting Grant 334840

History

Email Address of Submitting Author

jerome.waser@epfl.ch

Institution

Ecole Polytechnique Federale de Lausanne

Country

Switzerland

ORCID For Submitting Author

0000-0002-4570-914X

Declaration of Conflict of Interest

no conflict of interest

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