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

Manuel R RodríguezÁlvaro BeltránÁngel L MudarraEleuterio ÁlvarezFeliu MaserasM Mar Díaz-RequejoPedro J Pérez
Published in: Angewandte Chemie (International ed. in English) (2017)
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 TpBr3 Cu(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.
Keyphrases
  • electron transfer
  • crystal structure
  • ionic liquid
  • amino acid