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

doi:10.1002/anie.201705664

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

32 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 language	English
Pages (from-to)	12842-12847
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	42
DOIs	https://doi.org/10.1002/anie.201705664
Publication status	Published - 9 Oct 2017

Keywords

alkyne functionalization
copper catalysis
isothiazoles
nitrene transfer
sulfinamides

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

abstract = "{\textcopyright} 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.",

keywords = "alkyne functionalization, copper catalysis, isothiazoles, nitrene transfer, sulfinamides",

author = "Rodr{\'i}guez, {Manuel R.} and {\'A}lvaro Beltr{\'a}n and Mudarra, {{\'A}ngel L.} and Eleuterio {\'A}lvarez and Feliu Maseras and D{\'i}az-Requejo, {M. Mar} and P{\'e}rez, {Pedro J.}",

year = "2017",

month = oct,

day = "9",

doi = "10.1002/anie.201705664",

language = "English",

volume = "56",

pages = "12842--12847",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles

AU - Rodríguez, Manuel R.

AU - Beltrán, Álvaro

AU - Mudarra, Ángel L.

AU - Álvarez, Eleuterio

AU - Maseras, Feliu

AU - Díaz-Requejo, M. Mar

AU - Pérez, Pedro J.

PY - 2017/10/9

Y1 - 2017/10/9

N2 - © 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.

AB - © 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.

KW - alkyne functionalization

KW - copper catalysis

KW - isothiazoles

KW - nitrene transfer

KW - sulfinamides

U2 - 10.1002/anie.201705664

DO - 10.1002/anie.201705664

M3 - Article

SN - 1433-7851

VL - 56

SP - 12842

EP - 12847

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 42

ER -

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

Abstract

Keywords

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