Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles

Manuel R. Rodríguez, Álvaro Beltrán, Ángel L. Mudarra, Eleuterio Álvarez, Feliu Maseras, M. Mar Díaz-Requejo, Pedro J. Pérez

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17 Citations (Scopus)

Abstract

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A novel transformation is reported for the reaction of terminal or internal alkynes with the nitrene precursor PhI=NTs (Ts=p-toluenesulfonyl) in the presence of catalytic amounts of TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5-tribromo-pyrazolylborate). Two products containing an imine functionality have been isolated from the reaction mixtures, identified as sulfinamides and isothiazoles. The former correspond to the formal reduction of the sulfone group into sulfoxide, whereas the latter involves the insertion of an alkyne carbon atom into the aromatic ring of the N-tosyl moiety.
Original languageEnglish
Pages (from-to)12842-12847
JournalAngewandte Chemie - International Edition
Volume56
Issue number42
DOIs
Publication statusPublished - 9 Oct 2017

Keywords

  • alkyne functionalization
  • copper catalysis
  • isothiazoles
  • nitrene transfer
  • sulfinamides

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