4.8 Article

Metal-Free Reductive Cleavage of C-N and S-N Bonds by Photoactivated Electron Transfer from a Neutral Organic Donor

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 2, Pages 474-478

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201306543

Keywords

electron transfer; cleavage reactions; photochemistry; radical ions; reduction

Funding

  1. ORSAS
  2. EPSRC
  3. University of Strathclyde
  4. EPSRC [EP/I501177/1] Funding Source: UKRI
  5. Engineering and Physical Sciences Research Council [EP/I501177/1] Funding Source: researchfish

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A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a)ArCNR and b)ArNC bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation.

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