RT Journal Article
T1 Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles
A1 Ramírez Rodríguez, Manuel
A1 Beltrán Martín, Álvaro
A1 Mudarra, Ángel L.
A1 Álvarez, Eleuterio
A1 Maseras, Feliu
A1 Díaz Requejo, María Mar
A1 Pérez Romero, Pedro José
AB 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 Tp(Br3)Cu(NCMe) (Tp(Br3)=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.
PB Wiley
SN 1433-7851
SN 1521-3773 electrónico
YR 2017
FD 2017
LK http://hdl.handle.net/10272/16196
UL http://hdl.handle.net/10272/16196
LA eng
NO Rodríguez, M. R., Beltrán, Á., Mudarra, Á. L., Álvarez, E., Maseras, F., Díaz-Requejo, M. M., & Pérez, P. J. (2017). Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles. Angewandte Chemie, 129(42), 13022–13027. https://doi.org/10.1002/ange.201705664
NO Support for this work was provided by the MINECO (CTQ2014-52769-C3-R-1, CTQ2014-57761-R, Severo Ochoa Excellence Accreditation 2014-2018 SEV-2013-0319, Red Intecat CTQ2014-52974-REDC) and by a FPU fellowship (M.R.R.). We thank Prof. Antonio Echavarren for helpful comments and discussions.
DS Repositorio Institucional de la Universidad de Huelva
RD 30 may 2026