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

Adam J. Pearce, Xin Yi See, Ian A. Tonks

Research output: Contribution to journalArticle

18 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6891-6894
Number of pages4
JournalChemical Communications
Volume54
Issue number50
DOIs
StatePublished - Jan 1 2018

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