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

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
› Author Affiliations
Further Information

Publication History

Received: 01 March 2013

Accepted: 17 March 2013

Publication Date:
24 April 2013 (eFirst)

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

 
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