Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade† †Electronic supplementary information (ESI) available: Full experimental details, NMR spectra, CCDC numbers for X-ray structures. CCDC 1570504, 1570698. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc04723a

نویسندگان

  • Mindaugas Šiaučiulis
  • Selma Sapmaz
  • Alexander P. Pulis
  • David J. Procter
چکیده

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.

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Institut des Sciences et Ingénierie Chim Lausanne (EPFL), 1015 Lausanne, Switzerla Université de Toulouse et CNRS INSA, UPS, Rangueil, 31077 Toulouse, France Department of Chemistry and Pharmacy, I University Erlangen-Nürnberg, Egerlandstra † Electronic supplementary information ( experimental details, NMR spectra, and CIF format. CCDC 1535285–1535289. Fo or other electronic format see DOI: 10....

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عنوان ژورنال:

دوره 9  شماره 

صفحات  -

تاریخ انتشار 2018