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Issue 50, 2018
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Oxidative nitrene transfer from azides to alkynes via Ti(II)/Ti(IV) redox catalysis: formal [2+2+1] synthesis of pyrroles

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Abstract

Catalytic oxidative nitrene transfer from azides with the early transition metals is rare, and has not been observed without the support of redox noninnocent spectator ligands. Here, we report the formal [2+2+1] coupling of azides and alkynes via TiII/TiIV redox catalysis from simple Ti halide imido precatalysts. These reactions yield polysubstituted N-alkyl pyrroles, including N-benzyl protected pyrroles and rare examples of very electron rich pentaalkyl pyrroles. Mechanistic analysis reveals that [2+2+1] reactions with bulky azides have different mechanistic features from previously-reported reactions using azobenzene as a nitrene source.

Graphical abstract: Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: formal [2+2+1] synthesis of pyrroles

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Publication details

The article was received on 03 Apr 2018, accepted on 17 May 2018 and first published on 17 May 2018


Article type: Communication
DOI: 10.1039/C8CC02623H
Citation: Chem. Commun., 2018,54, 6891-6894
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    Oxidative nitrene transfer from azides to alkynes via Ti(II)/Ti(IV) redox catalysis: formal [2+2+1] synthesis of pyrroles

    A. J. Pearce, X. Y. See and I. A. Tonks, Chem. Commun., 2018, 54, 6891
    DOI: 10.1039/C8CC02623H

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