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Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade

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Abstract

A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement.

Graphical abstract: Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade

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Publication details

The article was received on 01 Nov 2017, accepted on 17 Nov 2017 and first published on 17 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC04723A
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade

    M. Šiaučiulis, S. Sapmaz, A. P. Pulis and D. J. Procter, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04723A

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