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

Rodríguez, Manuel R.; Beltrán Martín, Álvaro; Mudarra, Ángel L.; Álvarez, Eleuterio; Maseras, Feliu; Díaz Requejo, María Mar; Pérez Romero, Pedro José

doi:10.1002/anie.201705664

Author

Rodríguez, Manuel R.; Beltrán Martín, Álvaro; Mudarra, Ángel L.; Álvarez, Eleuterio; Maseras, Feliu; [et al.]
Publication Date

2017
Publisher

Wiley
Citation

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
Abstract

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.
URI

http://hdl.handle.net/10272/16196
Project

info:eu-repo/grantAgreement/MINECO (Severo Ochoa Excellence Accreditation) [2014-2018 SEV-2013-0319]
info:eu-repo/grantAgreement/MINECO (Red Intecat) [CTQ2014-52974-REDC]info:eu-repo/grantAgreement/MINECO [CTQ2014-52769-C3-R-1 and CTQ2014-57761-R]

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

Author

Rodríguez, Manuel R.; Beltrán Martín, Álvaro UHU Authority

; Mudarra, Ángel L.; Álvarez, Eleuterio; Maseras, Feliu; [et al.]

Publication Date

2017

Publisher

Wiley

Citation

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

Abstract

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.

URI

http://hdl.handle.net/10272/16196

Project

info:eu-repo/grantAgreement/MINECO (Severo Ochoa Excellence Accreditation) [2014-2018 SEV-2013-0319]
info:eu-repo/grantAgreement/MINECO (Red Intecat) [CTQ2014-52974-REDC]info:eu-repo/grantAgreement/MINECO [CTQ2014-52769-C3-R-1 and CTQ2014-57761-R]

Fichero	Tamaño	Formato	Ver	Description
Catalytic Nitrene.pdf	931.4Kb	PDF	View/Open	versión post-print

Fichero	Tamaño	Formato	Ver	Description
Catalytic Nitrene.pdf	931.4Kb	PDF	View/Open	versión post-print