Synthesis 2013; 45(19): 2699-2705
DOI: 10.1055/s-0033-1338419
special topic
© Georg Thieme Verlag Stuttgart · New York

Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis

Authors

  • Megan A. Cismesia

    Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706, USA   Fax: +1(608)2654534   Email: tyoon@chem.wisc.edu
  • Michael A. Ischay

    Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706, USA   Fax: +1(608)2654534   Email: tyoon@chem.wisc.edu
  • Tehshik P. Yoon*

    Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706, USA   Fax: +1(608)2654534   Email: tyoon@chem.wisc.edu
Further Information

Publication History

Received: 01 March 2013

Accepted: 17 March 2013

Publication Date:
24 April 2013 (online)


Graphical Abstract

Abstract

We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.

Supporting Information