Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor

Steven O'Sullivan; Eswararao Doni; Tell Tuttle; John A Murphy

doi:10.1002/anie.201306543

Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor

Angew Chem Int Ed Engl. 2014 Jan 7;53(2):474-8. doi: 10.1002/anie.201306543. Epub 2013 Dec 6.

Authors

Steven O'Sullivan¹, Eswararao Doni, Tell Tuttle, John A Murphy

Affiliation

¹ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK).

Abstract

A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a) ArCNR and b) ArNC 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.

Keywords: cleavage reactions; electron transfer; photochemistry; radical ions; reduction.

© 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.