4.6 Article

Weak O-Assistance Outcompeting Strong N,N-Bidentate Directing Groups in Copper Catalyzed C-H Chalcogenation

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 25, Pages 8475-8478

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601821

Keywords

C-H activation; copper; selenylation; sulfenylation; triazoles

Funding

  1. Alexander von Humboldt-foundation
  2. European Research Council under European Community [307535]
  3. European Research Council (ERC) [307535] Funding Source: European Research Council (ERC)

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A copper-mediated C-H chalcogenation of triazoles has been achieved by weak coordination. The user-friendly protocol showed high functional-group tolerance and ample substrate scope, yielding fully substituted 1,2,3-triazoles with complete positional site-selectivity. The C-H selenylation could likewise be achieved by means of copper catalysis. Our findings highlight for the first time that weak O-coordination can outcompete the strong N,N-bidentate coordination mode in C-H functionalization technology.

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