Issue 50, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Eph 2018
Accepted
17 Mey 2018
First published
17 Mey 2018

Chem. Commun., 2018,54, 6891-6894

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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