Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four-Membered Sulfur-Containing Cycles

Raffaele Senatore, Monika Malik, Thierry Langer, Wolfgang Holzer, Vittorio Pace (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

A formal CH2−CH2 homologation conducted with C1 carbenoids on a carbon electrophile for the obtainment of a four-membered cycle is reported. The logic proposes the consecutive delivery of two single nucleophilic CH2 units to an isothiocyanate—as competent electrophilic partner—resulting in the assembling of a rare imino-thietane cluster. The single synthetic operation procedure documents genuine chemocontrol, as indicated by the tolerance to various reactive elements decorating the starting materials. Significantly, the double homologation protocol is accomplished directly on a carbon electrophile, thus not requiring the installation of heteroatom-centered manifolds (e.g. boron).

Original languageEnglish
Pages (from-to)24854-24858
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number47
DOIs
Publication statusPublished - 15 Nov 2021

Austrian Fields of Science 2012

  • 104015 Organic chemistry

Keywords

  • carbenoids
  • chemoselectivity
  • homologation
  • isothiocyanates
  • thietanes

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