ol0c00561_si_001.pdf (13.29 MB)
Iron-Catalyzed Reductive Vinylation of Tertiary Alkyl Oxalates with Activated Vinyl Halides
journal contribution
posted on 2020-02-24, 21:03 authored by Yang Ye, Haifeng Chen, Ken Yao, Hegui GongWe
present herein a rare and efficient method for the creation
of vinylated all carbon quaternary centers via Fe-catalyzed cross-electrophile
coupling of vinyl halides with tertiary alkyl methyl oxalates. The
reaction displays excellent functional group tolerance and broad substrate
scope, which allows cascade radical cyclization and vinylation to
afford complex bicyclic and spiral structural motifs. The reaction
proceeds via tertiary alkyl radicals, and the putative vinyl–Br/Fe
complexation appears to be crucial for activating the alkene and enabling
a possibly concerted radical addition/C–Fe forming process.
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motifbicycliccreationalkenealkyl methyl oxalatesreaction displayssubstrate scopevinyl halidescyclizationspiralcascadeTertiary Alkyl OxalatesmethodActivated Vinyl Halidescomplexationreaction proceedsgroup tolerancecarbon quaternary centersvinylationIron-Catalyzed Reductive Vinylationalkyl radicalsFe-catalyzed cross-electrophilevinylated
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