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

Megan A. Cismesia; Michael A. Ischay; Tehshik P. Yoon

doi:10.1055/s-0033-1338419

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2699-2705
DOI: 10.1055/s-0033-1338419

special topic

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

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Abstract

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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.

Key words

electron transfer - heterocycles - hydroxamic acids - photochemistry - reduction

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References

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